Aromatic amine derivative and organic electroluminescence device using the same

ABSTRACT

An aromatic amine derivative with a specific structure having a carbazole skeleton to which a diarylamino group bonds via a bonding group. An organic electroluminescence device which is composed of one or more organic thin film layers including at least one light emitting layer sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers contains the aromatic amine derivative singly or as its mixture component. Organic electroluminescence devices with enhanced efficiency of light emission and a compound realizing the devices are provided.

The present application is a Continuation application of Ser. No.11/928,907, allowed, which claims priority to JP 2006-317093 having afiling date of Nov. 24, 2006 and JP 2007-211117 having a filing date ofAug. 13, 2007.

TECHNICAL FIELD

The present invention relates to an aromatic amine derivative and anorganic electroluminescence device using the derivative. Moreparticularly, it relates to an organic electroluminescence device withan enhanced efficiency of light emission and a novel aromatic aminederivative realizing the device.

BACKGROUND ART

An organic electroluminescence (“electroluminescence” will beoccasionally referred to as “EL”, hereinafter) device is a spontaneouslight emitting device which utilizes the phenomenon that a fluorescentsubstance emits light by energy of recombination of holes injected froman anode and electrons injected from a cathode when an electric field isapplied. Since an organic EL device of the laminate type driven under alow electric voltage was reported by C. W. Tang et al. of Eastman KodakCompany (C. W. Tang and S. A. Vanslyke, Applied Physics Letters, Volume51, Page 913, 1987), many studies have been conducted on organic ELdevices using organic materials as the constituting materials. Tang etal. used tris(8-quinolinolato)aluminum for the light emitting layer anda triphenyldiamine derivative for the hole transporting layer.Advantages of the laminate structure are that the efficiency of holeinjection into the light emitting layer can be increased, that theefficiency of forming excitons which are formed by blocking andrecombining electrons injected from the cathode can be increased, andthat the excitons formed in the light emitting layer can be confined. Asthe structure of the organic EL device, a two-layered structure having ahole transporting (injecting) layer and an electron transporting andlight emitting layer and a three-layered structure having a holetransporting (injecting) layer, a light emitting layer and an electrontransporting (injecting) layer are well known. To increase theefficiency of recombination of injected holes and electrons in thedevices of the laminate type, the structure of the device and theprocess for forming the device have been studied.

Conventionally, aromatic diamine derivatives described in PatentDocument 1 below and aromatic diamine derivatives with fused ringsdescribed in Patent Document 2 below have been known as holetransporting materials for the organic EL devices.

As improved compounds, Patent Documents 3 to 5 disclose arylamine-basedcompounds containing carbazole, which are employed as hole transportingmaterials. Further, Patent Document 6 discloses an arylamine-basedcompound having 3-position-substituted carbazole {e.g. Compound (A)below}, which is employed as a hole injecting material. Although someimprovements in an efficiency of light emission or so are achieved inthe devices employing those compounds into a hole injecting layer or ahole transporting layer, the efficiency of light emission is notsufficient yet and further enhancement of the efficiency of lightemission was required.

Furthermore, although Patent Document 7 discloses arylamine-basedcompounds having 3-position substituted carbazole {e.g. Compound (B)below}, they are employed as a phosphorescent host material, withoutreporting any embodiment of employing them as a hole injecting materialor a hole transporting material in the past.

Moreover, although Patent Document 8 discloses compounds wherein3-position substituted carbazole bonds to amine via a phenylene group,there were problems that the compounds have an elevated vapor depositiontemperature and that the efficiency of light emission was small. Therewas a shortcoming in Compound 24 disclosed in Patent Document 9 that ithad a short device lifetime. Further, there was also a shortcoming inCompound 40 disclosed in Patent Document 9 that it had an elevated vapordeposition temperature.

-   Patent Document 1: U.S. Pat. No. 4,720,432-   Patent Document 2: U.S. Pat. No. 5,061,569-   Patent Document 3: U.S. Pat. No. 6,242,115-   Patent Document 4: JP 11-144873A-   Patent Document 5: JP 2000-302756A-   Patent Document 6: JP 2006-151979A-   Patent Document 7: JP 2005-290000A-   Patent Document 8: JP 2003-133075A-   Patent Document 9: JP 2004-079265A

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

The present invention has been made to overcome the above problems andhas an object of providing an organic EL device having an enhancedefficiency of light emission, and an object of providing a compoundrealizing the EL device.

Means for Solving the Problem

As a result of intensive researches and studies to achieve the aboveobject by the present inventors, it was found that an employment of anaromatic amine derivative having a carbazole skeleton bonding with adiarylamino group via a bonding group as a material for the organic ELdevice, especially as a hole transporting material or a hole injectingmaterial for the organic EL device enables to produce an organic ELdevice having an enhanced efficiency of light emission, resultantlycompleting the present invention. Because the compound of the presentinvention has an effect of blocking electrons from a neighboring layerin an electron transporting layer side resulting as Ea (Electronaffinity) becoming shallow compared with the compound having structuresof the above (A), (B) or so, it is considered that a recombinationefficiency rises and an efficiency of light emission enhances.

Namely, the present invention provides an aromatic amine derivativerepresented by the following general formula (1);

(In the formula, L₁ represents a substituted or unsubstituted arylenegroup having 6 to 60 carbon atoms forming the aromatic ring, asubstituted or unsubstituted fluorenylene group, or a substituted orunsubstituted heteroarylene group having 5 to 60 atoms forming a ring;Ar₁ and Ar₂ each independently represents a substituted or unsubstitutedaryl group having 6 to 60 carbon atoms forming the aromatic ring or asubstituted or unsubstituted heteroaryl group having 5 to 60 atomsforming a ring; R₁ represents a substituted or unsubstituted aryl grouphaving 6 to 60 carbon atoms forming the aromatic ring; R₂ represents ahydrogen atom, a substituted or unsubstituted aryl group having 6 to 60carbon atoms forming the aromatic ring, a substituted or unsubstitutedalkyl group having 1 to 50 carbon atoms, a substituted or unsubstitutedalkoxy group having 1 to 50 carbon atoms, a substituted or unsubstitutedaryloxy group having 1 to 50 atoms forming a ring, a substituted orunsubstituted arylthio group having 5 to 50 atoms forming a ring, asubstituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbonatoms, an amino group substituted by a substituted or unsubstituted arylgroup having 5 to 50 carbon atoms forming the aromatic ring, a halogenatom, a cyano group, a nitro group, a hydroxyl group or a carboxylgroup; with the proviso that neither Ar₁ nor Ar₂ contains a fluorenestructure, and that the number of a carbazole structure in the aromaticamine derivative represented by the general formula (1) is 1 or 2.)

Further, the present invention provides an organic EL device which iscomposed of one or more organic thin film layers including at least onelight emitting layer and sandwiched between a cathode and an anode,wherein at least one of the organic thin film layers contains thearomatic amine derivative singly or in combination of two or more.

Effect of the Invention

The organic EL device employing the aromatic amine derivative of thepresent invention as a material for the organic EL device has anenhanced efficiency of light emission.

PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION

The present invention provides an aromatic amine derivative representedby the following general formula (1):

In the general formula (1), L₁ represents a substituted or unsubstitutedarylene group having 6 to 60 (preferably 6 to 18) carbon atoms formingthe aromatic ring, a substituted or unsubstituted fluorenylene group, ora substituted or unsubstituted heteroarylene group having 5 to 60(preferably 5 to 20) atoms forming a ring.

Examples of the arylene group and the heteroarylene group represented byL₁ include divalent groups of phenyl group, 1-naphthyl group, 2-naphthylgroup, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthrylgroup, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group,9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group,9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group,2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group,p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group,m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group,p-(2-phenylpropy)phenyl group, 3-methyl-2-naphthyl group,4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylylgroup, 4″-t-butyl-p-terphenyl 4-yl group, fluoranthenyl group, fluorenylgroup, 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinylgroup, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group,1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group,5-indolyl group, 6-indolyl group, 7-indolyl group, 1-iso indolyl group,2-iso indolyl group, 3-iso indolyl group, 4-iso indolyl group, 5-isoindolyl group, 6-iso indolyl group, 7-iso indolyl group, 2-furyl group,3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group,4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group,7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group,4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranylgroup, 7-isobenzofuranyl group, quinolyl group, 3-quinolyl group,4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group,8-quinolyl group, 1 isoquinolyl group, 3-isoquinolyl group,4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group,7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group,5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group,2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolylgroup, 1-phenanthridinyl group, 2-phenanthridinyl group,3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinylgroup, 7-phenanthridinyl group, 8-phenanthridinyl group,9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group,2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinylgroup, 1,7-phenanthroline-2-yl group, 1,7-phenanthroline-3-yl group,1,7-phenanthroline-4-yl group, 1,7-phenanthroline-5-yl group,1,7-phenanthroline-6-yl group, 1,7-phenanthroline-8-yl group,1,7-phenanthroline-9-yl group, 1,7-phenanthroline-10-yl group,1,8-phenanthroline-2-yl group, 1,8-phenanthroline-3-yl group,1,8-phenanthroline-4-yl group, 1,8-phenanthroline-5-yl group,1,8-phenanthroline-6-yl group, 1,8-phenanthroline-7-yl group,1,8-phenanthroline-9-yl group, 1,8-phenanthroline-10-yl group,1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3-yl group,1,9-phenanthroline-4-yl group, 1,9-phenanthroline-5-yl group,1,9-phenanthroline-6-yl group, 1,9-phenanthroline-7-yl group,1,9-phenanthroline-8-yl group, 1,9-phenanthroline-10-yl group,1,10-phenanthroline-2-yl group, 1,10-phenanthroline-3-yl group,1,10-phenanthroline-4-yl group, 1,10-phenanthroline-5-yl group,2,9-phenanthroline-1-yl group, 2,9-phenanthroline-3-yl group,2,9-phenanthroline-4-yl group, 2,9-phenanthroline-5-yl group,2,9-phenanthroline-6-yl group, 2,9-phenanthroline-7-yl group,2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10-yl group,2,8-phenanthroline-1-yl group, 2,8-phenanthroline-3-yl group,2,8-phenanthroline-4-yl group, 2,8-phenanthroline-5-yl group,2,8-phenanthroline-6-yl group, 2,8-phenanthroline-7-yl group,2,8-phenanthroline-9-yl group, 2,8-phenanthroline-10-yl group,2,7-phenanthroline-1-yl group, 2,7-phenanthroline-3-yl group,2,7-phenanthroline-4-yl group, 2,7-phenanthroline-5-yl group,2,7-phenanthroline-6-yl group, 2,7-phenanthroline-8-yl group,2,7-phenanthroline-9-yl group, 2,7-phenanthroline-10-yl group,1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group,2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group,10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group,3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group,2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolylgroup, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group,3-thienyl group, 2-methylpyrrole-1-yl group, 2-methylpyrrole-3-yl group,2-methylpyrrole-4-yl group, 2-methylpyrrole-5-yl group,3-methylpyrrole-1-yl group, 3-methylpyrrole-2-yl group,3-methylpyrrole-4-yl group, 3-methylpyrrole-5-yl group,2-t-butylpyrrole-4-yl group, 3-(2-phenylpropyl)pyrrole-1-yl group,2-methyl-1 indolyl group, 4-methyl-1 indolyl group, 2-methyl-3-indolylgroup, 4-methyl-3-indolyl group, 2-t-butyl-1-indolyl group,4-t-butyl-1-indolyl group, 2-t-butyl-3-indolyl group,4-t-butyl-3-indolyl group, etc.

Preferable examples of the arylene group represented by L₁ includephenylene group, biphenylene group, terphenylene group, quarterphenylenegroup, naphthylene group, anthracenylene group, phenanthrylene group,chrycenylene group, pyrenylene group, perilenylene group, fluorenylenegroup, etc. Preferable examples are phenylene group, biphenylene group,terphenylene group, fluorenylene group, naphthylene group,phenanthrylene group. Further preferable examples are phenylene group,biphenylene group, terphenylene group, naphthylene, group,phenanthrylene group or fluorenylene group.

Preferable heteroarylene groups are divalent groups of thiophenylylgroup, 1-phenylthiophenylyl group, 1,4-diphenylthiophenylyl group,benzthiophenylyl group, 1-phenylbenzothiophenylyl group,1,8-diphenylbenzothiophenylyl group, furyl group,1-phenyldibenzothiophenylyl group, 1,8-diphenylthiophenylyl group,dibenzofuranyl group, 1-phenyldibenzofuranyl group,1,8-diphenyldibenzofuranyl group, benzothiazolyl group, etc. Furtherpreferable heteroarylene groups are divalent groups of1-phenylthiophenylyl group, 1-phenylbenzothiophenylyl group,1-phenyldibenzofuranyl group, benzothiazolyl group, etc.

In the general formula (1), A₁ and Ar₂ each independently represents asubstituted or unsubstituted aryl group having 6 to 60 (preferably 6 to18) carbon atoms forming the aromatic ring or a substituted orunsubstituted heteroaryl group having 5 to 60 (preferably 5 to 20) atomsforming a ring; with the proviso that neither A₁ nor Ar₂ contains afluorene structure.

Examples of the aryl group represented by A₁ or Ar₂ include phenylgroup, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group,2-anthracenyl group, 9-anthracenyl group, 1-phenanthryl group,2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group,9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group,9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group,2-biphenyl group, 3-biphenylyl group, 4-biphenylyl group,p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group,m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,etc.

Examples of the heteroaryl group represented by A₁ or Ar₂ includemonovalent group or so of the hetero arylene group represented by theabove L₁.

In a general formula (1), R₁ represents a substituted or unsubstitutedaryl group having 6 to 60 (preferably 6 to 18) carbon atoms forming thearomatic ring.

Examples of the aryl group represented by the above R₁ include phenylgroup, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group,2-anthracenyl group, 9-anthracenyl group, 1-phenanthryl group,2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group,9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group,9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group,2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group,p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group,m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group,p-(2-phenylpropyl)phenyl group, 3-methyl-2-naphthyl group,4-methyl-1-naphthyl group, 4-methyl-1-anthryl group,4′-methylbiphenyl-yl group, 4″-t-butyl-p-terphenyl-4-yl group, etc.Preferable examples are phenyl group, 1-naphthyl group, 2-naphthylgroup, 4-biphenylyl group, p-terphenyl-4-yl group and more preferableexamples are phenyl group, biphenylyl group, terphenylyl group,α-naphthyl, group, β-naphthyl group and phenanthryl group.

In the general formula (1), R₂ represents a hydrogen atom, a substitutedor unsubstituted aryl group having 6 to 60 (preferably 6 to 30) carbonatoms forming the aromatic ring, a substituted or unsubstituted alkylgroup having 1 to 50 (preferably 1 to 20) carbon atoms, a substituted orunsubstituted alkoxy group having 1 to 50 (preferably 1 to 20) carbonatoms, a substituted or unsubstituted aryloxy group having 6 to 50(preferably 6 to 20) atoms forming a ring, a substituted orunsubstituted arylthio group having 5 to 50 (preferably 6 to 20) atomsforming a ring, a substituted or unsubstituted alkoxycarbonyl grouphaving 2 to 50 (preferably 2 to 20) carbon atoms, an amino groupsubstituted by a substituted or unsubstituted aryl group having 6 to 50(preferably 6 to 20) carbon atoms forming the aromatic ring, a halogenatom, a cyano group, a nitro group, a hydroxyl group or a carboxylgroup.

In the general formula (1), it is preferable that R₂ corresponds to asubstituted or unsubstituted aryl group having 6 to 60 carbon atomsforming the aromatic ring bonded to 3- or 6-position of a carbazoleskeleton.

Examples of the aryl group represented by R₂ include phenyl group,1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenylgroup, 9-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group,3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group,1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group,1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group,3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group,p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group,m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolylgroup, p-tolyl group, p-t-butylphenyl group, p-(2-phenylpropyl)phenylgroup, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group,4-methyl-1-anthryl group, 4′-methylbiphenyl-yl group,4″-t-butyl-p-terphenyl-4-yl group, fluorenyl group, etc. Preferableexamples are phenyl group, 1-naphthyl group, 2-naphthyl group,4-biphenylyl group, p-terphenyl-4-yl, group, p-tolyl group and fluorenylgroup.

Examples of the alkyl group represented by R₂ include methyl group,ethyl group, iso-propyl group, tert-butyl group, n-octyl group, n-decylgroup, n-hexadecyl group, cyclopropyl group, cyclopentyl group,cyclohexyl group, vinyl group, allyl group, 2-butenyl group, 3-pentenylgroup, propargyl group, 3-pentynyl group, etc. Preferable examples aremethyl group, ethyl group, iso-propyl group, tert-butyl, group,cyclopentyl group and cyclohexyl group.

Examples of the alkoxy group represented by R₂ include methoxy group,ethoxy group, n-propoxy group, iso-propoxy group, n-butoxy group,tert-butoxy group, etc. Preferable examples are methoxy group, ethoxygroup and tert-butoxy group.

Examples of the aryloxy group represented by R₂ include phenyloxy group,1-naphthyloxy group, 2-naphthyloxy group, 4-biphenylyloxy group,p-terphenyl-4-yloxy group, p-tolyloxy group, etc. Preferable examplesare phenyloxy group and 2-naphthyloxy group.

Examples of the arylthio group represented by R₂ include phenylthiogroup, 1-naphthylthio group, 2-naphthylthio group, 4-biphenylylthiogroup, p-terphenyl-4-ylthio group, p-tolylthio group, etc. Preferableexamples are phenylthio group and 2-naphthylthio group.

Examples of the alkoxycarbonyl group represented by R₂ includemethoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group,iso-propoxycarbonyl group, n-butoxycarbonyl group, tert-butoxycarbonylgroup, etc. Preferable examples are methoxycarbonyl group andethoxycarbonyl group.

Examples of the amino group substituted by the aryl group represented byR₂ include an amino group substituted by the aryl group represented byR₁, etc.

Examples of the amino group represented by R₂ include amino group,methylamino group, dimethylamino group, diethylamino group,dibenzylamino group, etc. Preferable examples are dimethylamino groupand diethylamino group.

Examples of the halogen atom represented by R₂ include fluorine atom,chlorine atom, bromine atom, iodine atom, etc.

Further, R₂ is preferably a hydrogen atom, a phenyl group, a biphenylylgroup, a terphenylyl group, an α-naphthyl group, a β-naphthyl group, amethyl group, an ethyl group, a propyl group, an isopropyl group, anarylamino group, etc.

Each these groups may be further substituted, and when there are two ormore groups, they may be the same with or different from each other.Moreover, in a case where it is possible, they may couple each other toform a ring.

Examples of substituents for each groups of Ar₁, Ar₂, R₁ and R₂ include,alkyl group (alkyl group preferably having 1 to 20 carbon atoms, morepreferably having 1 to 12 carbon atoms and particularly preferablyhaving 1 to 8 carbon atoms; examples include methyl, ethyl, iso-propyl,tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl,cyclohexyl, etc.); alkenyl group (alkenyl group preferably having 2 to20 carbon atoms, more preferably having 2 to 12 carbon atoms andparticularly preferably having 2 to 8 carbon atoms; examples includevinyl, allyl, 2-butenyl, 3-pentenyl, etc.); alkynyl group (alkynyl grouppreferably having 2 to 20 carbon atoms, more preferably having 2 to 12carbon atoms and particularly preferably having 2 to 8 carbon atoms;examples include propargyl, 3-pentynyl, etc.); amino group (amino grouppreferably having 0 to 20 carbon atoms, more preferably having 0 to 12carbon atoms and particularly preferably having 0 to 6 carbon atoms;examples include amino, methylamino, dimethylamino, diethylamino,diphenylamino, dibenzylamino, etc.); alkoxy group (alkoxy grouppreferably having 1 to 20 carbon atoms, more preferably having 1 to 12carbon atoms and particularly preferably having 1 to 8 carbon atoms;examples include methoxy, ethoxy, butoxy, etc.); aryloxy group (aryloxygroup preferably having 6 to 20 carbon atoms, more preferably having 6to 16 carbon atoms and particularly preferably having 6 to 12 carbonatoms; examples include phenyloxy, 2-naphthyloxy, etc.); acyl group(acyl group preferably having 1 to 20 carbon atoms, more preferablyhaving 1 to 16 carbon atoms and particularly preferably having 1 to 12carbon atoms; examples include acetyl, benzoyl, formyl, pivaloyl, etc.);alkoxycarbonyl group (alkoxycarbonyl group preferably having 2 to 20carbon atoms, more preferably having 2 to 16 carbon atoms andparticularly preferably having 2 to 12 carbon atoms; examples includemethoxycarbonyl, ethoxycarbonyl, etc.); aryloxycarbonyl group(aryloxycarbonyl group preferably having 7 to 20 carbon atoms, morepreferably having 7 to 16 carbon atoms and particularly preferablyhaving 7 to 10 carbon atoms; examples include phenyloxycarbonyl, etc.);acyloxy group (acyloxy group preferably having 2 to 20 carbon atoms,more preferably having 2 to 16 carbon atoms and particularly preferablyhaving 2 to 10 carbon atoms; examples include acetoxy, benzoyloxy,etc.); acylamino group (acylamino group preferably having 2 to 20 carbonatoms, more preferably having 2 to 16 carbon atoms and particularlypreferably having 2 to 10 carbon atoms; examples include acetylamino,benzoylamino, etc.); alkoxycarbonylamino group (alkoxycarbonylaminogroup preferably having 2 to 20 carbon atoms, more preferably having 2to 16 carbon atoms and particularly preferably having 2 to 12 carbonatoms; examples include methoxycarbonylamino, etc.);aryloxycarbonylamino group (aryloxycarbonylamino group preferably having7 to 20 carbon atoms, more preferably having 7 to 16 carbon atoms andparticularly preferably having 7 to 12 carbon atoms; examples includephenyloxycarbonylamino, etc.); sulfonylamino group (sulfonylamino grouppreferably having 1 to 20 carbon atoms, more preferably having 1 to 16carbon atoms and particularly preferably having 1 to 12 carbon atoms;examples include methanesulfonylamino, benzensulfonylamino, etc.);sulfamoyl group (sulfamoyl group preferably having 0 to 20 carbon atoms,more preferably having 0 to 16 carbon atoms and particularly preferablyhaving 0 to 12 carbon atoms; examples include sulfamoyl,methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl, etc.); carbamoylgroup (carbamoyl group preferably having 1 to 20 carbon atoms, morepreferably having 1 to 16 carbon atoms and particularly preferablyhaving 1 to 12 carbon atoms; examples include carbamoyl,methylcarbamoyl, diethykarbamoyl, phenylcarbamoyl, etc.); alkylthiogroup (alkylthio group preferably having 1 to 20 carbon atoms, morepreferably having 1 to 16 carbon atoms and particularly preferablyhaving 1 to 12 carbon atoms; examples include methylthio, ethylthio,etc.); arylthio group (arylthio group preferably having 6 to 20 carbonatoms, more preferably having 6 to 16 carbon atoms and particularlypreferably having 6 to 12 carbon atoms; examples include phenylthio,etc.); sulfonyl group (sulfonyl group preferably having 1 to 20 carbonatoms, more preferably having 1 to 16 carbon atoms and particularlypreferably having 1 to 12 carbon atoms; examples include mesyl, tosyl,etc.); sulfonyl group (sulfinyl group preferably having 1 to 20 carbonatoms, more preferably having 1 to 16 carbon atoms and particularlypreferably having 1 to 12 carbon atoms; examples includemethanesulfinyl, benzenesulfinyl, etc.); ureide group (ureide grouppreferably having 1 to 20 carbon atoms, more preferably having 1 to 16carbon atoms and particularly preferably having 1 to 12 carbon atoms;examples include ureide, methylureide, phenylureide, etc.);phosphoricamide group (phosphoricamide group preferably having 1 to 20carbon atoms, more preferably having 1 to 16 carbon atoms andparticularly preferably having 1 to 12 carbon atoms; examples includediethylphosphoricamide, phenylphosphateamide, etc.); hydroxy group;mercapto group; halogen atom (for example, fluorine atom, chlorine atom,bromine atom and iodine atom); cyano group; sulfo group; carboxyl group;nitro group; hydroxamic acid group; sulfino group; hydrazino group;imino group; heterocyclic group (heterocyclic group preferably having 1to 30 carbon atoms, more preferably having 1 to 12 carbon atoms;examples of the hetero atom include nitrogen atom, oxygen atom, sulfuratom; specific examples of the heterocyclic group include imidazolyl,pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl,benziraidazolyl, benzothiazolyl, carbazolyl, etc.); silyl group (silylgroup preferably having 3 to 40 carbon atoms, more preferably having 3to 30 carbon atoms and particularly preferably having 3 to 24 carbonatoms; examples include trimethylsilyl, triphenylsilyl, etc.); etc.Those substituents may be further substituted. Furthermore, when thereare two or more substituents, the substituents may be the same with ordifferent from each other. Moreover, in a case where it is possible,they may bond each other to form a ring.

It is preferable for the aromatic amine derivative represented by thegeneral formula (1) of the present invention has a structure representedby the following general formulae (1-a), (1-b), (1-c), (1-d), (1-e) and(1-D.

In the general formula (1-a), L₁, Ar₁, Ar₂, R₁ and R₂ are the same asthose defined in the general formula (1) respectively, and specificexamples, preferable examples and substituents are almost the same asdescribed above. Further, A₁ and Ar₂ may be the same with or differentfrom each other.

In the general formula (1-b), L₁, Ar₁, R₁ and R₂ are the same as thosedefined in the general formula (1) respectively, and specific examples,preferable examples and substituents are almost the same as describedabove.

L₂ represents a substituted or unsubstituted arylene group having 6 to60 carbon atoms forming the aromatic ring, or a substituted orunsubstituted heteroarylene group having 5 to 60 atoms forming a ring;and specific examples, preferable examples and substituents are almostthe same as those described about the above L₁.

Ar₃ and Ar₄ each independently represents a substituted or unsubstitutedaryl group having 6 to 60 carbon atoms forming the aromatic ring; andspecific examples, preferable examples and substituents of the arylgroup are almost the same as those described about the above Ar₁; withthe proviso that neither Ar₃ nor Ar₄ contains a fluorene structure.

Ar₁, Ar₃ and Ar₄ may be the same with or different from each other.

In the general formula (1-c), L₁, R₁ and R₂ are the same as thosedefined in the general formula (1) respectively, and specific examples,preferable examples and substituents are almost the same as describedabove.

L₂ and L₃ each independently represents a substituted or unsubstitutedarylene group having 6 to 60 carbon atoms forming the aromatic ring, ora substituted or unsubstituted heteroarylene group having 5 to 60 atomsforming a ring; and specific examples, preferable examples andsubstituents are almost the same as those described about the above L₁.

Ar₃ to Ar₆ each independently represents a substituted or unsubstitutedaryl group having 6 to 60 ring carbon atom; and specific examples,preferable examples and substituents of the aryl group are almost thesame as those described about the above Ar₁; with the proviso that noneof Ar₃ to Ar₆ contains a fluorene structure.

Further, Ar₃ to Ar₆ may be the same with or different from each other.

In the general formula (1-d), L₁, R₁ and R₂ are the same as thosedefined in the general formula (1) respectively, and specific examples,preferable examples and substituents are almost the same as describedabove.

Ar₇ and Ar₆ each independently represents a substituted or unsubstitutedarylene group having 6 to 60 carbon atoms forming the aromatic ring or asubstituted or unsubstituted heteroarylene group having 5 to 60 atomsforming a ring; specific examples and preferable examples includedivalent groups of almost the same as those described about the aboveAr₁, and examples of the substituents also include the same as describedabove.

Ar₉ and Ar₁₀ each independently represents a substituted orunsubstituted aryl group having 6 to 60 carbon atoms forming thearomatic ring, or a substituted or unsubstituted heteroaryl group having5 to 60 atoms forming a ring; and specific examples, preferable examplesand substituents are almost the same as those described about the aboveAr₁; with the proviso that none of Ar₇ to Ar₁₀ contains a fluorenestructure.

Further, Ar₇ to Ar₁₀ may be the same with or different from each other.

In the general formula (1-e), L₁, R₁ and R₂ are the same as thosedefined in the general formula (1) respectively, and specific examples,preferable examples and substituents are almost the same as describedabove.

Ar₁₁ to Ar₁₄ each independently represents a substituted orunsubstituted arylene group having 6 to 60 carbon atoms forming thearomatic ring or a substituted or unsubstituted heteroarylene grouphaving 5 to 60 atoms forming a ring; specific examples and preferableexamples include divalent groups of almost the same as those describedabout the above Art, and examples of the substituents also include thesame as described above.

Ar₁₁ and Ar₁₄ each independently represents a substituted orunsubstituted aryl group having 6 to 60 carbon atoms forming thearomatic ring, or a substituted or unsubstituted heteroaryl group having5 to 60 atoms forming a ring; and specific examples, preferable examplesand substituents are almost the same as those described about the aboveAr₁; with the proviso that none of Ar₁₁ to Ar₁₆ contains a fluorenestructure.

Further, Ar₁₁ to Ar₁₆ may be the same with or different from each other.

In the general formula (1-f), L₁, Ar₁, R₁ and R₂ are the same as thosedefined in the general formula (1) respectively; L₂ represents asubstituted or unsubstituted arylene group having 6 to 60 carbon atomsforming the aromatic ring or a substituted or unsubstitutedheteroarylene group having 5 to 60 atoms forming a ring; R₃ represents asubstituted or unsubstituted aryl group having 6 to 60 carbon atomsforming the aromatic ring; R₄ represents a hydrogen atom, a substitutedor unsubstituted aryl group having 6 to 60 carbon atoms forming thearomatic ring, a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50carbon atoms, a substituted or unsubstituted aryloxy group having 6 to50 atoms forming a ring, a substituted or unsubstituted arylthio grouphaving 5 to 50 atoms forming a ring, a substituted or unsubstitutedalkoxycarbonyl group having 2 to 50 carbon atoms, an amino groupsubstituted by a substituted or unsubstituted aryl group having 6 to 50carbon atoms forming the aromatic ring, a halogen atom, a cyano group, anitro group, a hydroxyl group or a carboxyl group.

In the general formulae (1), (1-a), (1-b), (1-c), (1-d), (1-e) and(1-f), L₁ represents an unsubstituted arylene group having 6 to 60carbon atoms forming the aromatic ring, an unsubstituted fluorenylenegroup or an unsubstituted heteroarylene group having 5 to 60 atomsforming a ring; Ar₁ and Ar₂ each independently represents anunsubstituted aryl group having 6 to 60 carbon atoms forming thearomatic ring or an unsubstituted heteroaryl group having 5 to 60 atomsforming a ring; R₁ represents an unsubstituted aryl group having 6 to 60carbon atoms forming the aromatic ring; R₂ represents a hydrogen atom,an unsubstituted aryl group having 6 to 60 carbon atoms forming thearomatic ring or an unsubstituted alkyl group having 1 to 50 carbonatoms; and neither A₁ nor Ar₂ contains a fluorene structure. Further, itis preferable that the aromatic amine derivative represented by thegeneral formula (1), (1-a), (1-b), (1-c), (1-d), (1-e) or (1-f) has 1 or2 carbazole structures.

Moreover, in the general formulae (1), (1-a), (1-b), (1-c), (1-d), (1-e)and (1-f), it is preferable that Ar₁ to Ar₆, Ar₉, Ar₁₀ and Ar₁₅ to Ar₁₆each independently represents a substituted or unsubstituted phenylgroup, a biphenylyl group, a terphenylyl group, an α-naphthyl group, aβ-naphthyl group or a phenanthryl group; and that Ar₇, Ar₈ and Ar₁₁ toAr₁₄ each independently represents a substituted or unsubstitutedphenylene group, a biphenylylene group, a terphenylylene group, anaphthylene group or a phenanthrylene groups.

Specific examples of the aromatic amine derivative represented by thegeneral formula (1) of the present invention include the followingcompounds, though not limited thereto.

It is preferable that a number of the ring carbon atoms forming ringscontained in the aromatic amine derivative of the present invention are48 to 70.

It is preferable that the aromatic amine derivative of the presentinvention is a material for the organic EL devices, further preferableto be a hole transporting material for the organic EL devices.

It is preferable that the aromatic amine derivatives of the presentinvention are employed especially as materials for the organic ELdevices that emit bluish light.

The organic EL device of the present invention is composed of one ormore organic thin film layers including at least one light emittinglayer and sandwiched between a cathode and an anode, wherein at leastone of the organic thin film layers contains the aromatic aminederivative singly or in combination of two or more.

The above aromatic amine derivative includes preferable embodiments inthe aromatic amine derivative of the present invention explained in theforegoing description.

It is preferable that the organic thin film layer in the organic ELdevice of the present invention includes a hole transporting layer andthe hole transporting layer contains the aromatic amine derivative ofthe present invention. Moreover, it is also preferable that the organicthin film layer has a hole injecting layer and that the aromatic aminederivative of the present invention is contained in the hole injectinglayer.

Moreover, it is preferable for the organic EL device of the presentinvention, that the above organic thin film layers have a holetransporting layer and/or a hole injecting layer, and it is furtherpreferable that the aromatic amine derivative of the present inventionis employed in the hole transporting layer or a hole injecting layer asa main component.

Furthermore, it is preferable that the light emitting layer in theorganic EL device of the present invention contains an arylaminecompound and/or a styrylamine compound.

It is preferable that the fluorescent dopant is a compound selectedadjusting to a color of light emission from a group consisting of anamine-based compound, an aromatic compound, a chelate complex oftris(8-quinolinolat)aluminum complex or so, coumarin derivatives,tetraphenylbutadiene derivatives, bisstyrylarylene derivatives,oxadiazole derivatives, etc. Specific examples include an arylaminecompound and an aryldiamine compound; among these, a styrylaminecompound, a styryldiamine compound, an aromatic amine compound and anaromatic diamine compound are more preferable. Moreover, fusedpolycyclic aromatic compounds (except amine compound) are furthermorepreferable. Those fluorescent dopants may be employable singly or incombination of two or more.

Preferred styrylamine compounds and styryldiamine compounds arerepresented by the following general formula (A):

(In the formula, Ar₃ represents a group selected from phenyl group,naphthyl group, biphenyl group, terphenyl group, stilbene group anddistyrylaryl group; Ar₄ and Ar₅ each independently represents anaromatic hydrocarbon group having 6 to 20 carbon atoms; and Ar₃, Ar₄ andAr₅ may be substituted. p represents an integer of 1 to 4, andpreferably an integer of 1 or 2. Anyone of Ar₃ to Ar₅ is a groupcontaining a styryl group. It is further preferable that the styrylgroup substitutes at least one of Ar₄ and Ar₅.)

Examples of the aromatic hydrocarbon group having 6 to 20 carbon atomsinclude phenyl group, naphthyl group, anthranyl group, phenanthrylgroup, terphenyl group, etc.

Preferred aromatic amine compounds and aromatic diamine compounds arerepresented by the following general formula (B):

(In the formula, Ar₆ to Ar₈ each independently represents a substitutedor unsubstituted aryl group having 5 to 40 carbon atoms forming thearomatic ring. q represents an integer of 1 to 4, and preferably aninteger of 1 or 2.)

Examples of the aryl group having 5 to 40 carbon atoms forming thearomatic ring include phenyl group, naphthyl group, anthranyl group,phenanthryl group, pyrenyl group, coronyl group, biphenyl group,terphenyl group, pyrrolyl group, furanyl group, thiophenyl group,benzthiophenyl group, oxadiazolyl group, diphenylanthranyl group,indolyl group, carbazolyl group, pyridyl group, benzquinolyl group,fluoranthenyl group, acenaphthofluoranthenyl group, stilbene group,perilenyl group, crycenyl group, picenyl group, triphenylenyl group,rubicenyl group, benzanthracenyl group, phenylanthranyl group,bisanthracenyl group, or an aryl group represented by the followinggeneral formula (C) or (D); and preferably, naphthyl group, anthranylgroup, crycenyl group, pyrenyl group, or an aryl group represented bythe general formula (D).

(In the general formula (C), r represents an integer of 1 to 3.)

Additionally, preferable examples of the substituent for the above arylgroup include an alkyl group having 1 to 6 carbon atoms (an ethyl group,a methyl group, an i-propyl group, a n-propyl group, a s-butyl group, at-butyl group, a pentyl group, a hexyl group, a cyclopentyl group, acyclohexyl group, etc.); an alkoxy group having 1 to 6 carbon atoms (anethoxy group, a methoxy group, an i-propoxy group, a n-propoxy group, as-butoxy group, a t-butoxy group, a pentoxy group, a hexyloxy group, acyclo pentoxy group, a cyclohexyl oxy group, etc.); an aryl group having5 to 40 carbon atoms forming the aromatic ring; an amino groupsubstituted with an aryl group having 5 to 40 carbon atoms forming thearomatic ring; an ester group which has an aryl group having 5 to 40carbon atoms forming the aromatic ring; an ester group which has analkyl group having 1 to 6 carbon atoms; a cyano group; a nitro group;and a halogen atom, etc.

Preferable fused polycyclic aromatic compounds (except amine compound)include fused polycyclic aromatic compounds such as naphthalene,anthracene, phenanthrene, pyrene, coronene, biphenyl, terphenyl,pyrrole, furan, thiophene, benzothiophene, oxadiazole, indole,carbazole, pyridine, benzoquinoline, fluoranthene, benzofluoranthene,acenaphthofluoranthene, stilbene, perylene, chrysene, picene,triphenylene, rubicene, benzoanthracene, etc., and those derivatives.

Following is a description regarding a device structure about theorganic EL device of the present invention.

(I) Construction of the Organic EL Device

Typical examples of the construction in the organic EL device of thepresent invention are shown below.

(1) An anode/a light emitting layer/a cathode;

(2) An anode/a hole injecting layer/a light emitting layer/a cathode;

(3) An anode/a light emitting layer/an electron injecting layer/acathode;

(4) An anode/a hole injecting layer/a light emitting layer/an electroninjecting layer/a cathode;

(5) An anode/an organic semiconductor layer/a light emitting layer/acathode;

(6) An anode/an organic semiconductor layer/an electron barrier layer/alight emitting layer/a cathode;

(7) An anode/an organic semiconductor layer/a light emitting layer/anadhesion improving layer/a cathode;

(8) An anode/a hole injecting layer/a hole transporting layer/a lightemitting layer/an electron injecting layer/a cathode;

(9) An anode/an acceptor containing layer/a hole injecting layer/a holetransporting layer/a light emitting layer/an electron transportinglayer/an electron injecting layer/a cathode;

(10) An anode/an insulating layer/a light emitting layer/an insulatinglayer/a cathode;

(11) An anode/an inorganic semiconductor layer/an insulating layer/alight emitting layer/an insulating layer/a cathode;

(12) An anode/an organic semiconductor layer/an insulating layer/a lightemitting layer/an insulating layer/a cathode;

(13) An anode/an insulating layer/a hole injecting layer/a holetransporting layer/a light emitting layer/an insulating layer/a cathode;and

(14) An anode/an insulating layer/a hole injecting layer/a holetransporting layer/a light emitting layer/an electron injecting layer/acathode.

Among the above constructions, construction (8) is usually preferablethough not limited to.

Although the aromatic amine derivative of the present invention may beused to any organic thin film layer in the organic EL device, it isemployable in the light emitting region or the hole transporting region,and a preferable embodiment of employing it into the hole transportingregion, or a particularly preferable embodiment of employing it into ahole transporting layer will make crystallization of molecules hard tocause thereby enhancing yield of producing the organic EL device.

In the organic EL device of the present invention, the organic thin filmlayer preferably contains the aromatic amine derivative of the presentinvention in an amount of 30 to 100% by mole.

(II) Substrate which Transmits Light

In general, the organic EL device is fabricated on a substrate whichtransmits light. The substrate which transmits light is a substrate forsupporting the organic EL device and preferably a flat and smoothsubstrate having a light transmittance of 50% or greater to visiblelight of 400 to 700 nm.

As the substrate which transmits light, for example, glass plate andsynthetic resin plate are advantageously employed. Specific examples ofthe glass plate include soda ash glass, glass containing barium andstrontium, lead glass, aluminosilicate glass, borosilicate glass, bariumborosilicate glass and quartz. Specific examples of the synthetic resinplate include plate made of polycarbonate resins, acrylic resins,polyethylene telephthalate resins, polyether sulfide resins andpolysulfone resins.

(III) Anode

The anode in the organic EL device of the present invention has afunction of injecting holes into a hole transporting layer or a lightemitting layer, and it is effective that the anode has a work functionof 4.5 eV or greater. Specific examples of the material for the anodeinclude indium tin oxide alloy (ITO), tin oxide (NESA), indium-zincoxide alloy (IZO), gold, silver, platinum, copper, etc.

The anode can be prepared by forming a thin film of the electrodematerial described above in accordance with a process such as the vapordeposition process and the sputtering process.

When the light emitted from the light emitting layer is obtained throughthe anode, it is preferable that the anode has a transmittance of theemitted light greater than 10%. It is also preferable that the sheetresistivity of the anode is several hundreds Ω/□ or smaller. Thethickness of the anode is, in general, selected usually in the range offrom 10 nm to 1 μM and preferably in the range of from 10 to 200 nm.

(IV) Light Emitting Layer

In the organic EL device of the present invention, the light emittinglayer combines the following functions (1) to (3):

(1) The injecting function: the function of injecting holes from theanode or the hole injecting layer and injecting electrons from thecathode or the electron injecting layer when an electric field isapplied;

(2) The transporting function: the function of transporting the injectedcharges (electrons and holes) by the force of the electric field; and

(3) The light emitting function: the function of providing the field forrecombination of electrons and holes and promote the recombination toemit light.

Although there may be a difference between the capability of the holesbeing injected and the capability of the electrons being injected, andalthough there may be a difference between the transporting functionsexpressed by mobilities of the holes and the electrons, either one ofthe charges is preferable to be transferred.

As the process for forming the light emitting layer, a well-knownprocess such as the vapor deposition process, the spin coating processand the LB process can be employed. It is particularly preferable forthe light emitting layer to be a molecular deposit film. The moleculardeposit film is a thin film formed by the deposition of a materialcompound in the gas phase or a thin film formed by the solidification ofa material compound in a solution or liquid phase. In general, themolecular deposit film can be distinguished from the thin film formed inaccordance with the LB process (the molecular accumulation film) basedon the differences in the aggregation structure and higher orderstructures and functional differences caused by these structuraldifferences.

In addition, as disclosed in JP 57-51781A, the light emitting layer canalso be formed by dissolving a binder such as a resin and the materialcompounds into a solvent to prepare a solution, followed by forming athin film from the prepared solution in accordance with the spin coatingprocess or the like.

In the present invention, any well-known light emitting material otherthan the aromatic amine derivative of the present invention may becontained in the light emitting layer, or a light emitting layercontaining any other well-known light emitting material may be laminatedwith the light emitting layer containing the aromatic amine derivativeof the present invention, as long as the object of the present inventionis not adversely affected.

Light emitting materials to be used for the light emitting layertogether with the aromatic amine derivatives of the present inventionincludes, for example, anthracene, naphthalene, phenanthrene, pyrene,tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene,naphthaloperylene, perinone, phthaloperinone, naphthaloperinone,diphenylbutadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldazine,bisbenzooxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metalcomplex, aminoquinoline metal complex, benzoquinoline metal complex,imine, diphenylethylene, vinylanthracene, diaminecarbazol, pyran,thiopyran, polymethyne, merocyanine, imidazol chelate oxinoid compound,quinacridone, rubrene and fluorescent dye, but not limited thereto.

Preferable host materials to be used for the light emitting layertogether with the aromatic amine derivatives of the present inventioninclude compounds represented by following general formulae (i) to (xi).

An asymmetric anthracene represented by the following general formula(i):

(In the above formula, Ar represents a substituted or unsubstitutedfused aromatic group having 10 to 50 carbon atoms forming the aromaticring; Ar′ represents a substituted or unsubstituted aromatic grouphaving 6 to 50 carbon atoms forming the aromatic ring; X represents asubstituted or unsubstituted aromatic group having 6 to 50 carbon atomsforming the aromatic ring, a substituted or unsubstituted aromaticheterocyclic group having 5 to 50 atoms forming a ring, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted orunsubstituted aralkyl group having 6 to 50 carbon atoms, a substitutedor unsubstituted aryloxy group having 5 to 50 atoms forming a ring, asubstituted or unsubstituted arylthio group having 5 to 50 atoms forminga ring, a substituted or unsubstituted alkoxycarbonyl group having 1 to50 carbon atoms, a carboxyl group, a halogen atom, a cyano group, anitro group or a hydroxyl group; a, b and c each represents an integerof 0 to 4; n represents an integer of 1 to 3; with the proviso that whenn is an integer of 2 or greater, the plural groups within squarebrackets ([ ]) may be the same with or different from each other.)

An asymmetric monoanthracene derivative represented by the followinggeneral formula (II):

(In the formula, Ar¹ and Ar² each independently represents a substitutedor unsubstituted aromatic ring group having 6 to 50 carbon atoms formingthe aromatic ring; m and n each represents an integer of 1 to 4; withthe proviso that in a case where m=n=1 and each bonding position of Ar¹and Ar² to a benzene ring is bilaterally symmetric to each other, Ar¹ isdifferent from Ar²; and in a case where m or n represents an integer of2 to 4, m is different from n; R¹ to R₁₀ each independently represents ahydrogen atom, a substituted or unsubstituted aromatic group having 6 to50 carbon atoms forming the aromatic ring, a substituted orunsubstituted aromatic heterocyclic group having 5 to 50 atoms forming aring, a substituted or unsubstituted alkyl group having 1 to 50 carbonatoms, a substituted or unsubstituted cycloalkyl group, a substituted orunsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted orunsubstituted aralkyl group having 6 to 50 carbon atoms, a substitutedor unsubstituted aryloxy group having 5 to 50 atoms forming a ring, asubstituted or unsubstituted arylthio group having 5 to 50 atoms forminga ring, a substituted or unsubstituted alkoxycarbonyl group having 1 to50 carbon atoms, a substituted or unsubstituted silyl group, a carboxylgroup, a halogen atom, a cyano group, a nitro group and a hydroxylgroup.)

An asymmetric pyrene derivative represented by the following generalformula (iii):

[In the formula, Ar and Ar′ each represents a substituted orunsubstituted aromatic group having 6 to 50 carbon atoms forming thearomatic ring; L and L′ each represents a substituted or unsubstitutedphenylene group, a substituted or unsubstituted naphthalenylene group, asubstituted or unsubstituted fluorenylene group or a substituted orunsubstituted dibenzosilolylene group; m represents an integer of 0 to2, n represents an integer of 1 to 4, s represents an integer of 0 to 2and t represents an integer of 0 to 4; L or Ar is bonded to any one of1- to 5-positions of pyrene ring; and L′ or Ar′ is bonded to any one of6- to 10-positions of pyrene ring; with the proviso that when n+trepresents an even number, Ar, Ar′, L and L′ satisfy the followingconditions (1) or (2):(1) Ar≠Ar′ and/or L≠L′ (wherein * means that each group has a differentstructure)(2) when Ar=Ar′ and L=L′(2-1) m≠s, and/or n≠t, or(2-2) when m=s and n≠t,(2-2-1) L and L′, or the pyrene ring, are respectively bonded todifferent positions of Ar and Ar′, or(2-2-2) in the case where L and L′, or the pyrene ring, are respectivelybonded to the same position of Ar and Ar′, the case where L and L′, orAr and Ar′ are bonded to the 1- and 6-positions or 2- and 7-positions ofthe pyrene ring is excluded.]

An asymmetric anthracene derivative represented by the following generalformula (Iv):

(In the formula, A¹ and A² each independently represents a substitutedor unsubstituted fused aromatic ring group having 10 to 20 carbon atomsforming the aromatic ring; Ar¹ and Ar² each independently represents ahydrogen atom, or a substituted or unsubstituted aromatic ring grouphaving 6 to 50 carbon atoms forming the aromatic ring.

R¹ to R¹⁰ each independently represents a hydrogen atom, a substitutedor unsubstituted aromatic group having 6 to 50 carbon atoms forming thearomatic ring, a substituted or unsubstituted aromatic heterocyclicgroup having 5 to 50 atoms forming a ring, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group, a substituted or unsubstituted alkoxygroup having 1 to 50 carbon atoms, a substituted or unsubstitutedaralkyl group having 6 to 50 carbon atoms, a substituted orunsubstituted aryloxy group having 5 to 50 atoms forming a ring, asubstituted or unsubstituted arylthio group having 5 to 50 atoms forminga ring, a substituted or unsubstituted alkoxycarbonyl group having 1 to50 carbon atoms, a substituted or unsubstituted silyl group, a carboxylgroup, a halogen atom, a cyano group, a nitro group and a hydroxylgroup.

The number of each of Ar¹, Ar², R₉ and R₁₀ may be two or more, and twoneighboring groups thereof may form a saturated or unsaturated ringstructure; with the proviso that the groups at 9- and 10-positions ofthe central anthracene are not symmetrical with respect to the X-Yaxis.)

An anthracene derivative represented by the following general formula(v);

(In the formula, R¹ to R₁₀ each independently represents a hydrogenatom, an alkyl group, a cycloalkyl group, an aryl group which may besubstituted, an alkoxyl group, an aryloxy group, an alkylamino group, analkenyl group, an arylamino group or a heterocyclic group which may besubstituted; and b each represents an integer of 1 to 5, and when eachof a and b is 2 or greater, R₁'s or R₂'s may be the same or different,and R₁'s or R₂'s may bond each other to form a ring; each pair of R³ andR⁴, R⁵ and R⁶, R⁷ and R⁸, and R⁹ and R¹⁰ may bond each other to form aring; L¹ represents a single bond, —O—, —S—, —N(R)—, an alkylene groupor an arylene group wherein R represents an alkyl group or an aryl groupwhich may be substituted.)

An anthracene derivative represented by the following general formula(vi):

(In the formula, R¹¹ to R²⁰ each independently represents a hydrogenatom, an alkyl group, a cycloalkyl group, an aryl group, an alkoxylgroup, an aryloxy group, an alkylamino group, an arylamino group or aheterocyclic group which may be substituted; c, d, e and f eachrepresents an integer of 1 to 5, and when each of c, d, e and f is 2 orgreater, R₁₁'s, R¹²'s, R₁₆'s or R₁₇'s may be the same or different, andR₁₁'s, R₁₂'s, R₁₆'s or R₁₇'s may bond each other to form a ring; eachpair of R₁₃ and R₁₄, and R₁₈ and R¹⁹ may bond each other to form a ring;L₂ represents a single bond, —O—, —S—, —N(R)—, an alkylene group or anarylene group wherein R represents an alkyl group or an aryl group whichmay be substituted.)

A spirofluorene derivative represented by the following general formula(vii):

(In the formula, A⁵ to A⁸ each independently represents a substituted orunsubstituted biphenylyl group or a substituted or unsubstitutednaphthyl group.)

A compound containing a fused ring represented by a following generalformula (viii):

(In the formula, A⁹ to A¹⁴ are the same as described above, and R²¹ toR²³ each independently represents a hydrogen atom, an alkyl group having1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, analkoxyl group having 1 to 6 carbon atoms, an aryloxy group having 5 to18 carbon atoms, an aralkyloxy group having 7 to 18 carbon atoms, anarylamino group having 5 to 16 carbon atoms, a nitro group, a cyanogroup, an ester group having 1 to 6 carbon atoms or a halogen atom; andat least one of A⁹ to A¹⁴ represents a fused aromatic ring having 3 ormore rings.)

A fluorene compound represented by the following general formula (ix):

(In the formula, R₁ and R₂ each independently represents a hydrogenatom, a substituted or unsubstituted alkyl group, a substituted orunsubstituted aralkyl group, a substituted or unsubstituted aryl group,a substituted or unsubstituted heterocyclic group, a substituted aminogroup, a cyano group or a halogen atom; R₁'s and R₂'s bonding todifferent fluorene groups may be respectively the same or different, andR₁ and R₂ bonding to the same fluorene group may be the same ordifferent; R₃ and R₄ each independently represents a hydrogen atom, asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedaralkyl group, a substituted or unsubstituted aryl group, or asubstituted or unsubstituted heterocyclic group, and R₃'s and R₄'sbonding to different fluorene groups may be respectively the same ordifferent, and R₃ and R₄ bonding to the same fluorene group may be thesame or different; Ar₁ and Ar₂ each independently represents asubstituted or unsubstituted fused polycyclic aromatic group consistingof benzene rings of 3 or more or a substituted or unsubstituted fusedpolycyclic heterocyclic group consisting of benzene rings and heterorings of 3 or more in total; and further, A₁ and Ar₂ may be the samewith, or different from each other; and n represents an integer of 1 to10.)

A compound having anthracene central skeleton represented by thefollowing general formula (x):

(In the formula (x), A₁ and A₂ each independently represents a groupderived from a substituted or unsubstituted aromatic ring having 6 to 20carbon atoms. One or more substituents may substitute the aromatic ring.

The substituent is selected among a substituted or unsubstituted arylgroup having 6 to 50 carbon atoms forming the aromatic ring, asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 50 carbonatoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbonatoms, a substituted or unsubstituted aralkyl group having 6 to 50carbon atoms, a substituted or unsubstituted aryloxy group having 5 to50 atoms forming a ring, a substituted or unsubstituted arylthio grouphaving 5 to 50 atoms forming a ring, a substituted or unsubstitutedalkoxycarbonyl group having 1 to 50 carbon atoms, a substituted orunsubstituted silyl group, a carboxyl group, a halogen atom, a cyanogroup, a nitro group and a hydroxyl group.

When two or more substituents substitute the aromatic ring, thesubstituents may be the same with or different from each other, andadjacent substituents may bond each other to form a saturated orunsaturated cyclic structure.

R₁ to R₈ each independently selectively represents a hydrogen atom, asubstituted or unsubstituted aryl group having 6 to 50 carbon atomsforming the aromatic ring, a substituted or unsubstituted heteroarylgroup having 5 to 50 atoms forming a ring, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 carbon atoms, asubstituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, asubstituted or unsubstituted aralkyl group having 6 to 50 carbon atoms,a substituted or unsubstituted aryloxy group having 5 to 50 atomsforming a ring, a substituted or unsubstituted arylthio group having 5to 50 atoms forming a ring, a substituted or unsubstitutedalkoxycarbonyl group having 1 to 50 carbon atoms, a substituted orunsubstituted silyl group, a carboxyl group, a halogen atom, a cyanogroup, a nitro group and a hydroxyl group.)

A compound represented by the following general formula (xi) in which A₁and A₂ are groups different from each other defined in the above generalformula (x).

(In the formula (xi), A₁, A₂ and R₁ to R₈ each independently representsthe same as defined in the general formula (x) respectively; with theproviso that the groups at 9- and 10-positions of the central anthraceneare not symmetrical with respect to the X-Y axis.)

Among the above host materials, an anthracene derivative is preferableand a monoanthracene derivative is more preferable, further anasymmetric anthracene is particularly preferable.

In addition, a phosphorescent compound may be employed as a lightemitting material for dopant. A compound containing a carbazole ring fora host material is preferable as the phosphorescent compound. The dopantis not limited as long as it is a compound capable of emitting lightfrom triplet exciton, and preferably a metal complex containing at leastone metal selected from the group consisting of Ir, Ru, Pd, Pt, Os andRe, more preferably a porphyrin metal complex or an ortho-metallatedcomplex. A suitable host for phosphorescence composed of a compoundcontaining a carbazole ring is a compound having a function of makingthe phosphorescent compound to emit light by the energy transfer fromits excitation state to the phosphorescent compound. The host compoundis not limited as long as capable of transferring the exciton energy tothe phosphorescent compound and may be appropriately selected accordingto the purpose. The host compound may have any group such as a heteroring in addition to the carbazole ring.

Specific examples of the host compound include a carbazole derivative, atriazole derivative, an oxazole derivative, an oxadiazole derivative, animidazole derivative, a polyarylalkane derivative, a pyrazolinederivative, a pyrazlone derivative, a phenylenediamine derivative, anarylamine derivative, a calcone derivative substituted by amino group, astyrylanthracene derivative, a fluorenone derivative, a hydrazonederivative, a stilbene derivative, a silazane derivative, an aromatictertiary amine compound, a styrylamine compound, an aromaticdimethylidene compound, a porphyrin-based compound, ananthraquinodimethane derivative, an anthrone derivative, adiphenylquinone derivative, a thiopyrandioxide derivative, a carbodimidederivative, a fluorenylidene methane derivative, a distyrylpyrazinederivative, heterocyclic tetracarboxylic anhydride such as anaphthaleneperylene, a phthalocyanine derivative, various metal complexpolysilane compound such as a metal complex of 8-quinolinol derivativeand a metal complex having a ligand of metallophthalocyanine,benzoxazole or benzothiazole, an electrically conductive polymericoligomer such as a poly(N-vinylcarbazole) derivative, an anilinecopolymer, a thiophene oligomer and a polythiophene, polymer compoundsuch as a polythiophene derivative, a polyphenylene derivative, apolyphenylenevinylene derivative and a polyfluorene derivative. The hostcompound may be used alone or in combination of two or more.

More specific examples include the following:

The phosphorescent dopant is a compound capable of emitting light fromthe triplet exciton. The phosphorescent dopant is not restricted as longas it emits light from the triplet exciton, and preferably a metalcomplex containing at least one metal selected from the group consistingof Ir, Ru, Pd, Pt, Os and Re, more preferably a porphyrin metal complexor an ortho-metallated metal complex. As the porphyrin metal complex, aporphyrin platinum complex is preferable. The phosphorescent compoundmay be used alone or in combination of two or more.

There are various ligands to form the ortho-metallated metal complex,and preferred are 2-phenylpyridine derivatives, 7,8-benzoquinolinederivatives, 2-(2-thienyl)pyridine derivatives, 2-(1-naphthyl)pyridinederivatives, and 2-phenylquinoline derivatives, etc. The derivatives mayhave a substituent as occasion demands. In particular, a dopantintroduced with a fluorine atom or a trifluoromethyl group is preferablefor the blue light emission. In addition, a ligand other than the aboveligands such as acetylacetonate and picric acid may be introduced as aco-ligand.

The amount of the phosphorescent dopant in the light emitting layer maybe selected for the objective as appropriate without particularlyrestricted, and for example, it may be selected in the range of from 0.1to 70% by mass, preferably in the range of from 1 to 30% by mass. Theemission is faint and the advantage is not demonstrated when the amountis less than 0.1% by mass. The concentration quenching becomesnoticeable so that the device performance is deteriorated when theamount exceeds 70% by mass.

Further, the light emitting layer may contain a hole transportingmaterial, a electron transporting material or a polymer binder, ifnecessary.

The thickness of the light emitting layer is, in general, selected inthe range of from 5 to 50 nm, preferably in the range of from 7 to 50 nmand the most preferably in the range of from 10 to 50 nm. It is resultedin difficult to form the light emitting layer and to controlchromaticity thereof when the thickness is thinner than 5 nm, and it maybe resulted in possibility of elevating driving voltage when it exceeds50 nm.

(V) Hole Injecting and Transporting Layer (Hole Transporting Region)

The hole injecting and transporting layer is a layer which helps theinjection of holes into the light emitting layer and transports theholes to the light emitting region. The layer exhibits a great mobilityof holes and, in general, has an ionization energy as small as 5.6 eV orsmaller. For the hole injecting and transporting layer, a material whichtransports holes to the light emitting layer at a small strength of theelectric field is preferable. A material which exhibits, for example, amobility of holes of at least 10⁻⁴ cm²/V·sec under an electric field offrom 10⁴ to 10⁶ V/cm is preferable.

When the aromatic amine derivative of the present invention is employedin the hole transporting region, the hole injecting and transportinglayer may be composed of the aromatic amine derivative of the presentinvention alone or in combination with another material.

When the aromatic amine derivative of the present invention is employedin the hole transporting layer, other materials may be employed in thehole injecting layer, and when the aromatic amine derivative of thepresent invention is employed in the hole injecting layer, othermaterials may be employed in the hole transporting layer.

With regard to the material which may be employed for forming the holeinjecting and transporting layer in combination with the aromatic aminederivative of the present invention, any material having the foregoingpreferable properties is employed without particularly restricted, whichis selected from compounds commonly used as a hole transporting materialof photoconductive materials and compounds used for forming the holeinjecting and transporting layer of EL devices. In the presentinvention, a material capable of transporting holes and being employablein a transporting region is defined as a hole transporting material.

Specific examples include triazole derivatives (refer to U.S. Pat. No.3,112,197, etc.), oxadiazole derivatives (refer to U.S. Pat. No.3,189,447, etc.), imidazole derivatives (refer to JP-B 37-16096, etc.),polyarylalkane derivatives (refer to U.S. Pat. Nos. 3,615,402;3,820,989; 3,542,544, JP-B 45-555, JP-B 51-10983, JP 51-93224A, JP55-17105A, JP 56-4148A, JP 55-108667A, JP 55-156953A, JP 56-36656A,etc.), pyrazoline derivatives and pyrazolone derivatives (refer to U.S.Pat. Nos. 3,180,729; 4,278,746; JP 55-88064A, JP 55-88065A, JP49-105537A, JP 55-51086A, JP 56-80051A, JP 56-88141A, JP 57-45545A, JP54-112637A, JP 55-74546A, etc.), phenylenediamine derivatives (refer toU.S. Pat. No. 3,615,404; JP-B 51-10105, JP-B 46-3712, JP-B 47-25336, JP54-119925A, etc.), arylamine derivatives (refer to U.S. Pat. Nos.3,567,450; 3,240,597; 3,658,520; 4,232,103; 4,175,961; 4,012,376; JP-B49-35702, JP-B 39-27577, JP 55-144250A, JP 56-119132A, JP 56-22437A,German Patent No. 1,110,518, etc.), amino-substituted chalconederivatives (refer to U.S. Pat. No. 3,526,501, etc.), oxazolederivatives (disclosed in U.S. Pat. No. 3,257,203, etc.),styrylanthracene derivatives (refer to JP 56-46234A, etc.), fluorenonederivatives (refer to JP 54-110837A, etc.), hydrazone derivatives (referto U.S. Pat. No. 3,717,462, JP 54-59143A, JP 55-52063A, JP 55-52064A, JP55-46760A, JP 57-11350A, JP 57-148749A, JP 2-311591A, etc.), stilbenederivatives (refer to JP 61-210363A, JP 61-228451A, JP 61-14642A, JP61-72255A, JP 62-47646A, JP 62-36674A, JP 62-10652A, JP 62-30255A, JP60-93455A, JP 60-94462A, JP 60-174749A, JP 60-175052A, etc.), silazanederivatives (U.S. Pat. No. 4,950,950), polysilane-based polymer (JP2-204996A), aniline-based copolymer (JP 2-282263A), etc.

With regard to the material for the hole injecting and transportinglayer, the above materials are also employable, and porphyrin compounds(disclosed in JP 63-2956965A), aromatic tertiary amine compounds andstyryl amine compounds (refer to U.S. Pat. No. 4,127,412, JP 53-27033A,JP 54-58445A, JP 55-79450A, JP 55-144250A, JP 56-119132A, JP 61-295558A,JP 61-98353A, JP 63-295695A, etc.) are preferable and the aromatictertiary amine compounds are particularly preferable.

Further examples include, 4,4′-bis(N-(1-naphthyl)-N-phenylamino)biphenyl(NPD) which has 2 fused aromatic rings in its molecule described in U.S.Pat. No. 5,061,569 and4,4′,4″-tris(N-(3-methylphenyl)-N-phenylamino)triphenylamine (MTDATA)described in JP 4-308688A which includes three triphenylamine unitsconnected in a star burst configuration.

Besides, a compound with heterocyclic derivative structure having anitrogen atom expressed with a following general formula disclosed inJapanese Registered Patent No. 03571977 is also employable.

In the formula, R¹²¹ to R¹²⁶ each independently represents any one of asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedaryl group, a substituted or unsubstituted aralkyl group or asubstituted or unsubstituted heterocyclic group. However, R¹²¹ to R¹²⁶may be the same with or different from each other. Further, both R¹²¹and R¹²², both R¹²³ and R¹²⁴, both R¹²⁵ and R¹²⁶, both R¹²¹ and R¹²⁶,both R¹²² and R¹²³ or both R¹²⁴ and R¹²⁵ may form a fused ring).

Still further, a compound expressed with a following general formuladisclosed in US Patent Application Publication No. 2004/0113547 is alsoemployable.

(In the formula, R₁₃₁ to R₁₃₆ are substituents, and preferably, theyeach independently represents an electron withdrawing group such as acyano group, a nitro group, a sulfonyl group, a carbonyl group, atrifluoromethyl group, a halogen atom, etc.)

Typically exemplified as those materials, a material having an acceptorproperty is also employable as a hole injecting material. Specificexamples of those are the same as described above.

In addition to the above-mentioned aromatic dimethylidene compounddescribed as a material for the light emitting layer, inorganic compoundsuch as p-type Si and p-type SiC may be used as the material for thehole injecting and transporting layer.

To form the hole injecting and transporting layer, a thin film may beformed from the aromatic amine derivative of the present invention inaccordance with a well-known process such as the vacuum vapor depositionprocess, the spin coating process, the casting process and the LBprocess. Although the thickness of the hole injecting and transportinglayer is not particularly limited, the thickness is usually from 5 nm to5 μm. The hole injecting and transporting layer may be a single layermade of one or more kinds of materials mentioned above or may belaminated with another hole injecting and transporting layer made of adifferent material, as long as the hole injecting and transporting layercontains the aromatic amine derivative of the present invention in itshole transporting region.

An organic semiconductor layer which preferably has an electricconductance of 10⁻¹⁰ S/cm or greater may be provided to assist theinjection of holes or electrons into the light emitting layer. Examplesof the materials for the organic semiconductor layer includeelectrically conductive oligomers such as an oligomer having thiopheneand an oligomer having arylamine disclosed in JP 8-193191A; andelectrically conductive dendrimers such as a dendrimer having anarylamine dendrimer.

(VI) Electron Injecting and Transporting Layer

The electron injecting and transporting layer is a layer having a greatelectron mobility, which assists the injection of electrons into thelight emitting layer and transports them to a light emitting region.Among the electron injecting layers, the adhesion improving layer is alayer made of a material exhibiting excellent adhesion to the cathode.

Further, it is known that because the emitted light reflects on theelectrode (cathode in this case) in the organic EL device, the lighttaken out directly through the anode and the light taken out after thereflection on the electrode interferes each other. To utilize theinterference effect effectively, the thickness of the electrontransporting layer is appropriately selected from several nm to severalμm. When the film is thicker, the hole mobility is preferably at least10⁻⁵ cm²/V·s under an electric field of from 10⁴ to 10⁶ V/cm foravoiding the elevation of driving voltage.

As the material for the electron injecting layer, metal complexes of8-hydroxyquinoline or derivatives thereof and oxadiazole derivatives arepreferable. Examples of the metal complexes of 8-hydroxyquinoline andderivatives thereof include metal chelate oxinoid compounds includingchelates of oxine (in general, 8-quinolinol or 8-hydroxyquinoline), forexample, tris(8-quinolinol)aluminum.

Examples of the oxadiazole derivatives include an electron transfercompound represented by the following general formulae:

(In the formula, Ar¹, Ar², Ar³, Ar⁵, Ar⁶ and Ar⁹ may be the same ordifferent and each independently represents a substituted orunsubstituted aryl group; Ar⁴, Ar⁷ and Ar⁸ may be the same or differentand each independently represents a substituted or unsubstituted arylenegroup.)

Examples of aryl group include a phenyl group, a biphenyl group, ananthryl group, a perilenyl group and a pyrenyl group. Examples of thearylene group include a phenylene group, a naphthylene group, abiphenylene group, an anthrylene group, a perilenylene group, apyrenylene group, etc. Examples of the substituent include an alkylgroup having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbonatoms and a cyano group. The electron transfer compound is preferably athin-film forming compound.

Specific examples of the electron transfer compounds are shown below:

Further, materials shown by following general formulae (A) to (F) areemployable for the electron injecting layer and the electrontransporting layer.

A nitrogen-containing heterocyclic derivative represented by thefollowing general formula (A) or (B);

(In the general formulae (A) and (B), A¹ to A³ each independentlyrepresents a nitrogen atom or a carbon atom; Ar¹ in the general formula(A) represents a substituted or unsubstituted aryl group having 6 to 60carbon atoms forming the aromatic ring or a substituted or unsubstitutedheteroaryl group having 3 to 60 atoms forming a ring; Ar¹ in the generalformula (B) represents a divalent group of Ar¹ in the general formula(A); Are represents a hydrogen atom, a substituted or unsubstituted arylgroup having 6 to 60 carbon atoms forming the aromatic ring, asubstituted or unsubstituted heteroaryl group having 3 to 60 atomsforming a ring, a substituted or unsubstituted alkyl group having 1 to20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to20 carbon atoms or those divalent groups. At least one of Ar¹ and Ar²represents a substituted or unsubstituted fused ring group having 10 to60 ring carbon atoms, a substituted or unsubstituted monohetero fusedring group having 3 to 60 ring carbon atoms, or those divalent groups.

L¹, L² and L each independently represents a single bond, a substitutedor unsubstituted arylene group having 6 to 60 carbon atoms forming thearomatic ring, a substituted or unsubstituted heteroarylene group having3 to 60 atoms forming a ring or a substituted or unsubstitutedfluorenylene group.

R represents a hydrogen atom, a substituted or unsubstituted aryl grouphaving 6 to 60 carbon atoms forming the aromatic ring, a substituted orunsubstituted heteroaryl group having 3 to 60 atoms forming a ring, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, ora substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;n represents an integer of 0 to 5; when n is 2 or greater, Rs may be thesame or different and adjacent couple of Rs may bond to form acarbocyclic aliphatic ring or a carbocyclic aromatic ring.

R¹ represents a hydrogen atom, a substituted or unsubstituted aryl grouphaving 6 to 60 carbon atoms forming the aromatic ring, a substituted orunsubstituted heteroaryl group having 3 to 60 atoms forming a ring, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, ora substituted or unsubstituted alkoxy group having 1 to 20 carbon atomsor -L-Ar¹—Ar².)

A nitrogen-containing heterocyclic derivative represented by a followinggeneral formula (C):HAr-L-Ar¹—Ar²  (C)(In the formula, HAr represents a nitrogen-containing heterocyclic grouphaving 3 to 40 carbon atoms which may have a substituent; L represents asingle bond, an arylene group having 6 to 60 carbon atoms which may havea substituent, a heteroarylene group having 3 to 60 carbon atoms whichmay have a substituent; Ar¹ represents a divalent aromatic hydrocarbongroup having 6 to 60 carbon atoms which may have a substituent; and Ar₂represents an aryl group having 6 to 60 carbon atoms which may have asubstituent or a heteroaryl group having 3 to 60 carbon atoms which mayhave a substituent.)

A silacyclopentadiene derivative represented by a following generalformula (D):

(In the formula, X and Y each independently represents a saturated orunsaturated hydrorocarbon group having 1 to 6 carbon atoms, an alkoxygroup, an alkenyloxy group, an alkenyloxy group, a hydroxy group, asubstituted or unsubstituted aryl group, or a substituted orunsubstituted hetero ring, or X and Y represents a saturated orunsaturated ring by bonding to each other; R₁ to R₄ each independentlyrepresents a hydrogen atom, a halogen atom, a substituted orunsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group,an aryloxy group, a perfluoroalkyl group, a perfluoroalkoxy group, anamino group, an alkylcarbonyl group, an arylcarbonyl group, analkoxycarbonyl group, an aryloxycarbonyl group, an azo group, analkylcarbonyloxy group, an arylcarbonyloxy group, an alkoxycarbonyloxygroup, an aryloxycarbonyloxy group, a sulfinyl group, a sulfonyl group,a sulfanyl group, a silyl group, a carbamoyl group, an aryl group, ahetero ring group, an alkenyl group, an alkynyl group, a nitro group, aformyl group, a nitroso group, a formyloxy group, an isocyano group, acyanate group, an isocyanate group, a thiocyanate group, anisothiocyanate group, or a cyano group, or an adjacent pair of R₁ to R₄represents a substituted or unsubstituted fused ring.)

A borane derivative represented by the following general formula (E):

(In the formula, R₁ to R₈ and Z₂ each independently represents ahydrogen atom, a saturated or unsaturated hydrocarbon group, an aromaticgroup, a hetero ring group, substituted amino group, a substituted borylgroup, an alkoxy group or an aryloxy group; X, Y and Z₁ eachindependently represents a saturated or unsaturated hydrocarbon group,an aromatic group, a hetero ring group, substituted amino group, analkoxy group or an aryloxy group; substituents of Z₁ and Z₂ may bonds toeach other to form a fused ring; n represents an integer of 1 to 3; andwhen n is 2 or greater, Z₁'s may be different from each other; with theproviso that a case where n is 1, X, Y and R₂ are methyl groups and R₈is a hydrogen atom or a substituted boryl group and a case where n is 3and Z₁ is a methyl group are excluded.)

[In the formula, Q¹ and Q² each independently represents a ligandrepresented by the following general formula (G), L represents a halogenatom, a substituted or unsubstituted alkyl group, a substituted orunsubstituted cycloalkyl group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted heterocyclic group, —OR¹ whereinR₁ represents a hydrogen atom, a substituted or unsubstituted alkylgroup, a substituted or unsubstituted cycloalkyl group, a substituted orunsubstituted aryl group and a substituted or unsubstituted heterocyclicgroup; or a ligand represented by —O—Ga-Q³(Q⁴) wherein Q³ and Q⁴ are thesame as Q¹ and Q².]

[In the formula, rings A¹ and A² each represents a fused six-memberedaryl ring structure which may be substituted.]

The metal complex strongly characterizes n-type semiconductor and has alarge capability of the electron injection. Since the generation energyfor forming the metal complex is small, the bonding between the metaland the ligand is strong, to increase the fluorescence quantumefficiency of light emitting materials.

Specific examples of the substituents of rings A¹ and A² each formingthe ligand in the general formula (G) include halogen atom such aschlorine atom, bromine atom, iodine atom and fluorine atom; substitutedor unsubstituted alkyl group such as methyl group, ethyl group, propylgroup, butyl group, s-butyl group, t-butyl group, pentyl group, hexylgroup, heptyl group, octyl group, stearyl group, trichloromethyl group,etc.; substituted or unsubstituted aryl group such as phenyl group,naphthyl group, 3-methylphenyl group, 3-methoxyphenyl group,3-fluorophenyl group, 3-trichloromethylphenyl group,3-trifluoromethylphenyl group, 3-nitrophenyl group, etc.; substituted orunsubstituted alkoxy group such as methoxy group, n-butoxy group,t-butoxy group, trichloromethoxy group, trifluoroethoxy group,pentafluoropropoxy group, 2,2,3,3-tetrafluoropropoxy group,1,1,1,3,3,3-hexafluoro-2-propoxy group, 6-(perfluoroethyl)hexyloxygroup, etc.; substituted or unsubstituted aryloxy group such as phenoxygroup, p-nitrophenoxy group, p-t-butylphenoxy group, 3-fluorophenoxygroup, pentafluorophenyl group, 3-trifluoromethylphenoxy group, etc.;substituted or unsubstituted alkylthio group such as methylthio group,ethylthio group, t-butylthio group, hexylthio group, octylthio group,trifluoromethylthio group, etc.; substituted or unsubstituted arylthiogroup such as phenylthio group, p-nitrophenylthio group,p-t-butylphenylthio group, 3-fluorophenylthio group,pentafluorophenylthio group, 3-trifluoromethylphenylthio group, etc.;cyano group; nitro group; amino group; mono- or di-substituted aminogroups such as methylamino group, diethylamino group, ethylamino group,diethylamino group, dipropylamino group, dibutyl amino group,diphenylamino group, etc.; acylamino groups such asbis(acetoxymethyl)amino group, bis(acetoxyethyl)amino group,bis(acetoxypropyl)amino group, bis(acetoxybutyl)amino group, etc.;hydroxy group; siloxy group; acyl group; carbamoyl group such asmethylcarbamoyl group, dimethylcarbamoyl group, ethylcarbamoyl group,diethylcarbamoyl group, a propylcarbamoyl group, butyl carbamoyl group,a phenylcarbamoyl group, etc.; carboxylic acid group; sulfonic acidgroup; imido group; cycloalkyl group such as cyclopentyl group,cyclohexyl group, etc.; aryl group such as phenyl group, naphthyl group,biphenyl group, anthryl group, phenanthryl group, fluorenyl group,pyrenyl group, etc.; heterocyclic group such as pyridinyl group,pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group,indolinyl group, quinolinyl group, acridinyl group, pyrrolidinyl group,dioxanyl group, piperidinyl group, morpholidinyl group, piperazinylgroup, triazinyl group, carbazolyl group, furanyl group, thiophenylgroup, oxazolyl group, an oxadiazolyl group, a benzoxazolyl group, athiazolyl group, a thiadiazolyl group, benzothiazolyl group, triazolylgroup, imidazolyl group, benzimidazolyl group, pranyl group, etc. Theabove substituents may bond each other to form a six-membered aryl ringor hetero ring.

A preferred embodiment of the organic EL device of the present inventioncontains a reductive dopant in an electron transporting region or aninterfacial region between a cathode and an organic compound layer. Thereductive dopant is defined as the substance capable of reducing anelectron transporting compound. Accordingly, various compounds having aspecified reducing property may be employable and examples of thereductive dopant include at least one compound selected from alkalimetals, alkaline earth metals, rare earth metals, oxides of alkalimetals, halides of alkali metals, oxides of alkaline earth metals,halides of alkaline earth metals, oxides of rare earth metals, halidesof rare earth metals, organic complexes of alkali metals, organiccomplexes of alkaline earth metals, and organic complexes of rare earthmetals.

Examples of the preferable reductive dopant include at least one alkalimetal selected from a group consisting of Na (the work function: 2.36eV), K (the work function: 2.28 eV), Rb (the work function: 2.16 eV) andCs (the work function: 1.95 eV) or at least one alkaline earth metalsselected from a group consisting of Ca (the work function: 2.9 eV), Sr(the work function: 2.0 to 2.5 eV) and Ba (the work function: 2.52 eV).whose work function of 2.9 eV or smaller is particularly preferable.Among those, more preferable reductive dopants include at least one kindor more alkali metal selected from the group consisting of K, Rb and Cs,the latter Rb or Cs being further more preferable and the last Cs beingthe most preferable. Since those alkali metals have a particularly highreducing capability, the luminance is improved and the lifetime isprolonged by the addition thereof into an electron injection region in arelatively small amount. A combination of two or more alkali metals isalso preferably used as the reductive dopant having a work function of2.9 eV or smaller. A combination containing Cs such as Cs and Na, Cs andK, Cs and Rb and Cs, Na and K is particularly preferred. By combinedlycontaining Cs, the reducing capability is effectively performed, and theluminance is enhanced and the lifetime is prolonged in the organic ELdevice by the addition into the electron injection region.

In the present invention, an electron injecting layer made of anelectrically insulating material or a semiconductor may be furtherdisposed between the cathode and the organic layer. The electroninjecting layer enables to effectively prevent a leak of electriccurrent and to improve the electron injection property. As theelectrically insulating material, at least one metal compound selectedfrom the group consisting of chalcogenides of alkali metals,chalcogenides of alkaline earth metals, halides of alkali metals andhalides of alkaline earth metals is preferable. It is preferable thatthe electron injecting layer is constituted with the above metalcompound since the electron injecting property can be further improved.Preferable examples of the alkali metal chalcogenide include Li₂O, K₂O,Na₂S, Na₂Se and NA₂O. Preferable examples of the alkaline earth metalchalcogenide include CaO, BaO, SrO, BeO, BaS and CaSe. Preferableexamples of the alkali metal halide include LiF, NaF, KF, LiCl, KCl andNaCl. Preferable examples of the alkaline earth metal halide includefluorides such as CaF₂, BaF₂, SrF₂, MgF₂ and BeF₂ and halides other thanthe fluorides.

Examples of the semiconductor constituting the electron transportinglayer include oxides, nitrides and oxide nitrides containing at leastone element selected from Ba, Ca, Sr, Yb, Al, Ga, In, L₁, Na, Cd, Mg,Si, Ta, Sb and Zn, which are used singly or in combination of two ormore. It is preferable that the inorganic compound for constituting theelectron transporting layer is in the form of a crystallite or amorphousinsulating thin film. When the electron transporting layer isconstituted with the above insulating thin film, a more uniform thinfilm can be formed and defective pixels such as dark spots can bedecreased. Examples of the inorganic compound include chalcogenides ofalkali metals, chalcogenides of alkaline earth metals, halides of alkalimetals and halides of alkaline earth metals, which are described above.

(VII) Cathode

The cathode is formed from an electrode substance such as metal, alloy,electrically conductive compound or a mixture thereof each having asmall work function (4 eV or smaller) to ensure the electron injectioninto the electron injecting or transporting layer or a light emittinglayer. Examples of the electrode substance include sodium,sodium-potassium alloy, magnesium, lithium, magnesium-silver alloy,aluminum/aluminum oxide, -lithium alloy, indium, rare earth metal, etc.

The cathode is prepared by forming a thin film of the electrode materialdescribed above in accordance with a process such as the vapordeposition process and the sputtering process.

When the light emitted from the light emitting layer is taken out of thecathode, it is preferable that the cathode has a transmittance ofgreater than 10% to the emitted light.

It is also preferable that the sheet resistivity of the cathode isseveral hundreds Ω/□ or smaller and the thickness of the cathode is, ingeneral, selected from 10 nm to 1 μm and preferably from 50 to 200 nm.

(VIII) Insulating Layer

In general, an organic EL device tends to form defects in pixels due toleak and short circuit since an electric field is applied to ultra-thinfilms. To prevent the defects, a layer of an insulating thin film may beinserted between the pair of electrodes.

Examples of the material employed for the insulating layer includealuminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesiumoxide, magnesium oxide, magnesium fluoride, calcium oxide, calciumfluoride, aluminum nitride, titanium oxide, silicon oxide, germaniumoxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxideand vanadium oxide. Mixtures and laminates of the above compounds canalso be employed.

(IX) Fabrication Process of the Organic EL Device

The organic EL device of the present invention is fabricated, forexample, by forming an anode, a light emitting layer, an optional holeinjecting and transporting layer, an optional electron injecting andtransporting layer, and a cathode in accordance with the process usingthe materials each being described above. Alternatively, each layer maybe formed in a reverse order from the cathode to the anode.

An embodiment of the fabrication of an organic EL device having aconstruction of anode/hole injecting layer/light emitting layer/electroninjecting layer/cathode in this order on a light-transmitting substratewill be described in the following.

First, on a suitable light-emitting substrate, a thin film of an anodesubstance is formed so as to have a film thickness of 1 μm or thinner,preferably from 10 nm to 200 nm in accordance with a vapor depositionprocess, a sputtering process, etc. Then, a hole injecting layer isformed on the anode. The hole injecting layer can be formed inaccordance with the vacuum vapor deposition process, the spin coatingprocess, the casting process or the LB process, as described above. Thevacuum vapor deposition process is preferable because a uniform film canbe easily obtained and pinhole is little formed. When the hole injectinglayer is formed in accordance with the vacuum vapor deposition process,the conditions are preferably selected from the following ranges:temperature of deposition source: 50 to 450° C.; degree of vacuum: 10⁻⁷to 10⁻³ Torr; vapor deposition rate: 0.01 to 50 nm/s; temperature ofsubstrate: 50 to 300° C.; and film thickness: 5 nm to 5 μm; althoughdepending on the employed compound (material for hole injecting layer),the crystal structure and the recombination structure.

Subsequently, the light emitting layer is formed on the hole injectinglayer by depositing a thin film of the organic light emitting materialin accordance with the vacuum vapor deposition process, the sputteringprocess, the spin coating process or the casting process. The vacuumvapor deposition process is preferable because a uniform film can beeasily obtained and pinhole is little formed. When, the light emittinglayer is formed in accordance with the vacuum vapor deposition process,the conditions of the vacuum vapor deposition can be selected in thesame ranges as in the deposition of the hole injecting layer, althoughdepending on the compound to be used.

Next, the electron injecting layer is formed on the light emitting layerformed above. Similarly to the formation of the hole injecting layer andlight emitting layer, the electron injecting layer is preferably formedin accordance with the vacuum vapor deposition process, because auniform film is required. The conditions of the vacuum vapor depositioncan be selected from the same ranges as in the formation of the holeinjecting layer and light emitting layer.

Although the aromatic amine derivatives of the present invention dependon that they are contained in any layer among a light emitting region ora hole transporting region, it may be commonly vapor deposited togetherwith other materials. In addition, when the spin coating process isemployed, it may be contained therein by blending it with othermaterials.

Finally, the cathode is formed on the electron injecting layer, toobtain an organic EL device.

The cathode is made of a metal and can be formed in accordance with thevacuum vapor deposition process or the sputtering process. However, thevacuum vapor deposition process is preferably employed in order toprevent the underlying organic layers from being damaged during theformation of the film.

In the above fabrication of the organic EL device, the layers from theanode to the cathode are successively formed preferably in a singleevacuation operation.

The process for forming the layers in the organic EL device of thepresent invention is not particularly limited. A conventional processsuch as the vacuum vapor deposition process and the spin coating processor so can be employed. The organic thin film layer containing thecompound of the formula (1) included in the organic EL device of thepresent invention can be formed in accordance with the vacuum vapordeposition process, the molecular beam epitaxy process (the MBE process)or a known method of coating a solution of the compound such as thedipping process, the spin coating process, the casting process, the barcoating process and the roller coating process.

The thickness of each layer in the organic thin film layer in theorganic EL device of the present invention is not particularly limited.In general, an excessively thin layer tends to have defects such aspinholes, and an excessively thick layer requires a high applied voltageand results in decreasing the efficiency. Therefore, the thickness ispreferably from several nm to 1 μm.

The organic EL device emits light when a direct voltage of 5 to 40 V isapplied with the anode being + terminal and the cathode being −terminal. In the reverse polarity, no electric current flows and nolight is emitted upon the application of voltage. When an alternatingvoltage is applied, the uniform light emission is observed only in thepolarity where the anode is + and the cathode is −. The wave shape ofalternating voltage is not limited.

EXAMPLES

The present invention will be described in further detail with referenceto Examples, which does not limit the scope of the present inventionunless it goes beyond the gist of the invention.

Constitutional formulae of Intermediates 1 to 22 to be prepared inSyntheses 1 to 22 are as follows.

Synthesis 1 (Synthesis of Intermediate 1)

Blending 17.7 g of 9-phenyl carbazole, 6.03 g of potassium iodide, 7.78g of potassium iodate, 5.90 ml of sulfuric acid and ethanol, thereaction was allowed to proceed at 75° C. for 2 h.

The resultant solution was cooled, and adding tap water and ethylacetate, it was separated and extracted. Subsequently, an organic layerwas washed with sodium bicarbonate water and tap water and then, it wascondensed. Purifying the resultant crude product by means of a silicagelchromatography (toluene), vacuum dried the resultant solid to obtain21.8 g of white solid, which was analyzed by FD-MS (Field DesorptionMass Spectrum) and identified as Intermediate 1.

Synthesis 2 (Synthesis of Intermediate 2)

Under an atmospheric argon gas flow, dehydrated toluene and dehydratedether were added to 13.1 g of Intermediate 1, and the resultant solutionwas cooled down to −45° C. Dripping 25 ml of n-butyllithium hexanesolution (1.58 M), elevated the temperature up to −5° C. while stirringfor 1 h. Cooling down to −45° C. again, after slowly dripping 25 ml ofboronic acid triisopropyl ester, the reaction was allowed to proceed for2 h.

Returning to a room temperature, a 10% dilute hydrochloric acid solutionwas added and stirred, and an organic layer was extracted. After washingwith a saturated sodium chloride solution, it was dried over unhydratedsulfur trioxide magnesium, separated by filtration and condensed.Purifying the resultant solid by means of a silicagel chromatography(toluene), the solid was washed with n-hexane and vacuum dried to obtain7.10 g of solid, which was analyzed by FD-MS and identified asIntermediate 2.

Synthesis 3 (Synthesis of Intermediate 3)

Blending 21.8 g of Intermediate 1, 11.8 g of 4-bromophenyl boronic acid,1.38 g of Pd(PPh₃)₄, 21.9 g of sodium carbonate, tap water anddimethoxyethane, the reaction was allowed to proceed under refluxing for8 h.

The resultant solution was cooled down and the reacted solution wasfiltered, and a water layer prepared by separating the filtered residuethrough acetone was extracted with dichloromethane. The collectedfiltrate was separated and adding acetone and dichloromethane, theresultant solution was further separated. A water layer prepared byseparating the filtered residue through acetone was extracted withdichloromethane, and a collected organic layer was washed with water andcondensed. Purifying the resultant crude product by means of a silicagelchromatography (hexane dichloromethane=9:1), re-crystallized theresultant solid through toluene and methanol, vacuum dried to obtain4.18 g of white solid, which was analyzed by FD-MS and identified asIntermediate 3.

Synthesis 4 (Synthesis of Intermediate 4)

Under an atmospheric argon gas flow, dissolving 12.5 g of2-bromofluorene into 50 ml of acetic acid, 0.9 ml of sulfuric acid wasdripped and stirred at a room temperature for 10 min. Subsequently, 6.5g of iodine and 2.33 g of periodic acid were added and the reaction wasallowed to proceed at 80° C. for 6 h.

The resultant solution was cooled down, extracted through toluene andtap water. Subsequently, a toluene layer was washed with sodiumbicarbonate water, saturated sodium chloride solution and tap water, andthen dried over sodium sulfate. After the sodium sulfate was separatedby filtration, purifying the resultant solid by means of a silicagelchromatography (toluene), the solid was washed with n-hexane and vacuumdried to obtain 9.00 g of solid, which was analyzed by FD-MS andidentified as Intermediate 4.

Synthesis 5 (Synthesis of Intermediate 5)

Under an atmospheric argon gas flow, 9.00 g of Intermediate 4 and 0.35 gof benzyltriethylammonium chloride were placed into 25 ml of DMSO(dimethylsulfoxide) and 8 ml of 50 wt % NaOH aqueous solution andstirred at a room temperature for 10 min, and dripping 2.6 ml of methyliodide, the reaction was allowed to proceed at a room temperature for 3h.

The resultant solution was extracted through toluene and tap water,washed with saturated sodium chloride solution and tap water, andcondensed. Purifying by means of silicagel chromatography (n-hexane),vacuum dried to obtain 8.50 g of solid, which was analyzed by FD-MS andidentified as Intermediate 5.

Synthesis 6 (Synthesis of Intermediate 6)

Under an atmospheric argon gas flow, placing 20.0 g of Intermediate 5,11.5 g of N-phenyl-1-naphthylamine, 447 mg of copper iodide, 0.532 ml ofN,N′-dimethylethylenediamine, 7.22 g of t-butoxy sodium and dehydratedxylene, the reaction was allowed to proceed at 130° C. for 8 h.

The resultant solution was cooled down and after extracting the reactedsolution through 100 ml of toluene it was filtered through sellite, andwas condensed. Purifying the resultant crude product by means of asilicagel chromatography (hexane toluene=9:1), the resultant pale yellowsolid was washed with methanol, vacuum dried to obtain 16.0 g of whitesolid, which was analyzed by FD-MS and identified as Intermediate 6.

Synthesis 7 (Synthesis of Intermediate 7)

Under an atmospheric argon gas flow, blending 17.0 g of benzamide, 68.8g of 4-bromobiphenyl, 2.70 g of copper iodide, 40.8 g of potassiumcarbonate and diethylbenzene, the reaction was allowed to proceed at175° C. for 19 h.

The resultant solution was cooled down and adding tap water, the residuewas washed with acetone, methanol and tap water 3 times to obtain 55.0 gof benzamide compound of Intermediate 7.

Blending 55.0 g of benzamide compound of Intermediate 7, 26.3 g ofpotassium hydroxide, 25 ml of tap water and diethylbenzene, the reactionwas allowed to proceed at 175° C. for 5.5 h.

The resultant solution was cooled down and after adding tap water, itwas filtered, washed with acetone, methanol and tap water 3 times.

Purifying the resultant mixture by means of a short column (toluene),the resultant solid was washed with n-hexane and vacuum dried to obtain25.0 g of white solid, which was analyzed by FD-MS and identified asIntermediate 7.

Synthesis 8 (Synthesis of Intermediate 8)

Intermediate 8 was synthesized in the same manner as Intermediate exceptthat Intermediate 7 was employed instead of N-phenyl-1-naphthylamine.The resultant solid was analyzed by FD-MS and identified as Intermediate8.

Synthesis 9 (Synthesis of Intermediate 9)

Intermediate 9 was synthesized in the same manner as Intermediate 6except that 1-bromo-4-iodobenzene was employed instead of Intermediate5. The resultant solid was analyzed by FD-MS and identified asIntermediate 9.

Synthesis 10 (Synthesis of Intermediate 10)

Intermediate 10 was synthesized in the same manner as Intermediate 2except that Intermediate 9 was employed instead of Intermediate 1. Theresultant solid was analyzed by FD-MS and identified as Intermediate 10.

Synthesis 11 (Synthesis of Intermediate 11)

Under an atmospheric argon gas flow, blending 5.70 g of benzamide, 11.5g of 4-bromobiphenyl, 450 mg of copper iodide, 6.80 g of potassiumcarbonate and diethylbenzene, the reaction was allowed to proceed at175° C. for 10 h.

The resultant solution was cooled down and after adding tap water, itwas filtered and the residue was washed with acetone, methanol and tapwater 3 times to obtain 11.8 g of Intermediate 11.

Synthesis 12 (Synthesis of Intermediate 12)

Under an atmospheric argon gas flow, blending 11.8 g of Intermediate 11,16.8 g of 4-bromotriphenylamine, 414 mg of copper iodide, 6.2 g ofpotassium carbonate and diethylbenzene, the reaction was allowed toproceed at 175° C. for 15 h.

The resultant solution was cooled down and adding tap water, the residuewas washed with acetone, methanol and tap water 3 times to obtain 20.4 gof benzamide compound of Intermediate 12.

Blending 20.4 g of benzamide compound of Intermediate 12, 7.89 g ofpotassium hydroxide, 7.5 ml of tap water and diethylbenzene, thereaction was allowed to proceed at 175° C. for 5.5 h.

The resultant solution was cooled down and after adding tap water, itwas filtered, washed with acetone, methanol and tap water 3 times.Purifying the resultant mixture by means of a short column (toluene),the resultant solid was washed with n-hexane and vacuum dried to obtain9.65 g of yellowish white solid, which was analyzed by FD-MS andidentified as Intermediate 12.

Synthesis 13 (Synthesis of Intermediate 13)

Intermediate 13 was synthesized in the same manner as Intermediate 3except that phenyl boronic acid was employed instead of 4-bromophenylboronic acids. The resultant solid was analyzed by FD-MS and identifiedas Intermediate 13.

Synthesis 14 (Synthesis of Intermediate 14)

Intermediate 14 was synthesized in the same manner as Intermediate 1except that Intermediate 13 was employed instead of 9-phenyl carbazole.The resultant solid was analyzed by FD-MS and identified as Intermediate14.

Synthesis 15 (Synthesis of Intermediate 15)

Intermediate 15 was synthesized in the same manner as Intermediate 2except that Intermediate 14 was employed instead of Intermediate 1. Theresultant solid was analyzed by FD-MS and identified as Intermediate 15.

Synthesis 16 (Synthesis of Intermediate 16)

Intermediate 16 was synthesized in the same manner as Intermediate 7except that 4-bromotriphenylamine was employed instead of4-bromobiphenyl. The resultant solid was analyzed by FD-MS andidentified as Intermediate 16.

Synthesis 17 (Synthesis of Intermediate 17)

Under an atmospheric argon gas flow, blending 3.3 g of carbazole, 5.1 gof 4-bromo biphenyl, 231 mg of Pd₂(dba)₃, 325 mg of P(t-Bu)₃, 2.9 g oft-butoxysodium and toluene, the reaction was allowed to proceed at 80°C. for 4 h.

The resultant solution was cooled down and after adding toluene; it wasfiltered through sellite and was condensed. Purifying the resultantmixture by means of a silicagel chromatography(hexane:dichloromethane=6:1), the resultant solid was washed withn-hexane, vacuum dried to obtain 4.1 g of white solid, which wasanalyzed by FD-MS and identified as Intermediate 17.

Synthesis 18 (Synthesis of Intermediate 18)

Intermediate 18 was synthesized in the same manner as Intermediate 1except that Intermediate 17 was employed instead of 9-phenylcarbazole.The resultant solid was analyzed by FD-MS and identified as Intermediate18.

Synthesis 19 (Synthesis of Intermediate 19)

Intermediate 19 was synthesized in the same manner as Intermediate 2except that Intermediate 18 was employed instead of Intermediate 1. Theresultant solid was analyzed by FD-MS and identified as Intermediate 19.

Synthesis 20 (Synthesis of Intermediate 20)

Intermediate 20 was synthesized in the same manner as Intermediate 3except that Intermediate 18 was employed instead of Intermediate 1. Theresultant solid was analyzed by FD-MS and identified as Intermediate 20.

Synthesis 21 (Synthesis of Intermediate 21)

Intermediate 21 was synthesized in the same manner as Intermediate 3except that 4-bromo-4′-iodobiphenyl was employed instead of Intermediate1 and that Intermediate 19 was employed instead of 4-bromophenyl boronicacids. The resultant solid was analyzed by FD-MS and identified asIntermediate 21.

Synthesis 22 (Synthesis of Intermediate 22)

Intermediate 22 was synthesized in the same manner as Intermediate 12except that 1-bromonaphthalene was employed instead of4-bromotriphenylamine. The resultant solid was analyzed by FD-MS andidentified as Intermediate 22.

Synthesis Example 1 (Synthesis of Compound H1)

Under an atmospheric argon gas flow, 6.0 g of Intermediate 2, 8.6 g ofIntermediate 6, 404 mg of Pd(PPh₃)₄ was placed into 26 ml of 2M sodiumcarbonate aqueous solution and toluene, the reaction was allowed toproceed under refluxing for 4 h.

The resultant solution was cooled down and was filtered through sellite,and the filtrate was separated. An organic layer was washed with tapwater, purifying by means of a silicagel chromatography (toluene),re-precipitated (hexane, dichloromethane) the resultant solid threetimes. Washing the solid with n-hexane, vacuum dried to obtain 6.93 g ofyellowish white solid, which was analyzed by FD-MS and identified asCompound H1. Synthesis Example 2 (Synthesis of Compound H2)

Compound H2 was synthesized in the same manner as Synthesis of CompoundH1 in Synthesis Example 1 except that Intermediate 8 was employedinstead of Intermediate 6. The resultant solid was analyzed by FD-MS andidentified as Compound H2.

Synthesis Example 3 (Synthesis of Compound H3)

Compound H3 was synthesized in the same manner as Synthesis of CompoundH1 in Synthesis Example 1 except that Intermediate 10 was employedinstead of Intermediate 2 and that Intermediate 3 was employed insteadof Intermediate 6. The resultant solid was analyzed by FD-MS andidentified as Compound H3.

Synthesis Example 4 (Synthesis of Compound H4)

Under an atmospheric argon gas flow, blending 4.8 g ofN-phenyl-1-naphthylamine, 8.0 g of Intermediate 3, 231 mg of Pd₂(dba)₃,325 mg of P(t-Bu)₃, 2.9 g of tertialbutoxysodium and toluene, thereaction was allowed to proceed at 80° C. for 4 h.

The resultant solution was cooled down and after adding toluene, it wasfiltered through sellite and was condensed. Purifying the resultantmixture by means of a silicagel chromatography(hexane:dichloromethane=6:1), the resultant solid was washed withn-hexane, vacuum dried to obtain 8.96 g of yellowish white solid, whichwas analyzed by FD-MS and identified as Compound H4.

Synthesis Example 5 (Synthesis of Compound H5)

Compound H5 was synthesized in the same manner as Synthesis of CompoundH4 in Synthesis Example 4 except that Intermediate 7 was employedinstead of N-phenyl-1-naphthylamine. The resultant solid was analyzed byFD-MS and identified as Compound H15.

Synthesis Example 6 (Synthesis of Compound H6)

Compound H6 was synthesized in the same manner as Synthesis of CompoundH4 in Synthesis Example 4 except that Intermediate 12 was employedinstead of N-phenyl-1-naphthylamine. The resultant solid was analyzed byFD-MS and identified as Compound H6.

Synthesis Example 7 (Synthesis of Compound H7)

Compound H7 was synthesized in the same manner as Synthesis of CompoundH1 in Synthesis Example 1 except that Intermediate 15 was employedinstead of Intermediate 2. The resultant solid was analyzed by FD-MS andidentified as Compound H7.

Synthesis Example 8 (Synthesis of Compound H8)

Compound H8 was synthesized in the same manner as Synthesis of CompoundH4 in Synthesis Example 4 except that Intermediate 16 was employedinstead of N-phenyl-1-naphthylamine. The resultant solid was analyzed byFD-MS and identified as Compound H8.

Synthesis Example 9 (Synthesis of Compound H53)

Compound H53 was synthesized in the same manner as Synthesis of CompoundH4 in Synthesis Example 4 except that Intermediate 7 was employedinstead of N-phenyl-1-naphthylamine and that Intermediate 20 wasemployed instead of Intermediate 3. The resultant solid was analyzed byFD-MS and identified as Compound H53.

Synthesis Example 10 (Synthesis of Compound H55)

Compound H55 was synthesized in the same manner as Synthesis of CompoundH4 in Synthesis Example 4 except that Intermediate 22 was employedinstead of N-phenyl-1-naphthylamine. The resultant solid was analyzed byFD-MS and identified as Compound H55.

Synthesis Example 11 (Synthesis of Compound H57)

Compound H57 was synthesized in the same manner as Synthesis of CompoundH4 in Synthesis Example 4 except that aniline was employed instead ofN-phenyl-1-naphthylamine. The resultant solid was analyzed by FD-MS andidentified as Compound H57.

Synthesis Example 12 (Synthesis of Compound H60)

Compound H60 was synthesized in the same manner as Synthesis of CompoundH4 in Synthesis Example 4 except that Intermediate 7 was employedinstead of N-phenyl-1-naphthylamine and that Intermediate 21 wasemployed instead of Intermediate 3. The resultant solid was analyzed byFD-MS and identified as Compound H60.

Example 1

A glass substrate (manufactured by GEOMATEC Company) of 25 mm×75 mm×1.1mm thickness having an ITO transparent electrode was cleaned byapplication of ultrasonic wave in isopropyl alcohol for 5 min and thenby exposure to ozone generated by ultraviolet light for 30 min. Thecleaned glass substrate having the transparent electrode lines wasattached to a substrate holder of a vacuum vapor deposition apparatus.On the surface of the cleaned substrate at the side having thetransparent electrode, a film of Compound H232 below having a thicknessof 60 nm was formed so as to cover the transparent electrode. The formedfilm of H232 worked as the hole injecting layer. A layer of the CompoundH1 as a hole transporting material having a thickness of 20 nm wasformed over the film of H232. The formed film worked as the holetransporting layer. Further, Compound EM1 below was vapor depositedthereby forming a film having a thickness of 40 nm. At the same time,the following amine compound D1 having styryl group below as a lightemitting molecule was deposited with a weight ratio of EM1:D1=40:2. Theformed film worked as a light emitting layer. On the film formed above,a film of Alq having a thickness 10 nm was formed. The formed filmworked as an electron injecting layer. Thereafter, Li (the source oflithium: manufactured by SAES GETTERS Company) as a reductive dopant andAlq were binary vapor deposited and an Alq:Li film (film thickness: 10nm) was formed as the electron injecting layer (or the cathode). On theAlq:Li film, aluminum was vapor deposited to form a metal cathode and anorganic EL device was fabricated.

About the resultant organic EL device, luminescent color was observedand current efficiency of light emission was measured at initialluminance of 5000 cd/m² under a room temperature and DC constant currentdriving. The results are shown in Table 1.

Examples 2 to 12

Organic EL devices were fabricated in similar procedures as Example 1except that compounds described in Table 1 were employed as the holetransporting material instead of Compound Hi.

About the resultant organic EL devices, luminescent colors were observedand current efficiencies of light emission were measured at initialluminance of 5000 cd/m² under a room temperature and DC constant currentdriving. The results are shown in Table 1.

Comparative Examples 1 to 5

Organic EL devices were fabricated in similar procedures as Example 1except that Comparative Compounds 1 to 5 below and described in Table 1were employed as the hole transporting material instead of Compound H1.

About the resultant organic EL device, luminescent colors were observedand current efficiencies of light emission were measured at initialluminance of 5000 cd/m² under a room temperature and DC constant currentdriving. The results are shown in Table 1.

Example 13

An organic EL device was fabricated in a similar procedure as Example 1except that arylamine compound D2 below was employed instead of theamine compound D1 having styryl groups. Me represents a methyl group.

About the resultant organic EL device, luminescent color was observedand current efficiency of light emission was measured at initialluminance of 5000 cd/m² under a room temperature and DC constant currentdriving. The results are shown in Table 1.

Comparative Example 6

Organic EL device was fabricated in a similar procedure as Example 12except that the above Comparative Compound H1 was employed as the holetransporting material instead of Compound H1.

About the resultant organic EL device, luminescent color was observedand current efficiency of light emission was measured at initialluminance of 5000 cd/m² under a room temperature and DC constant currentdriving. The results are shown in Table 1.

TABLE 1 Emission Comparative efficiency Luminescent Examples Compounds(cd/A) color 1 H1 6.8 Blue 2 H2 6.9 Blue 3 H3 6.4 Blue 4 H4 5.9 Blue 5H5 6.1 Blue 6 H6 6.0 Blue 7 H7 7.1 Blue 8 H8 5.9 Blue 9  H53 6.7 Blue10   H55 6.5 Blue 11   H57 6.3 Blue 12   H60 6.8 Blue 13  H1 6.1 BlueEmission Comparative Comparative efficiency Luminescent ExamplesCompounds (cd/A) color 1 1 5.1 Blue 2 2 4.0 Blue 3 3 4.3 Blue 4 4 4.8Blue 5 5 3.9 Blue 6 1 5.2 Blue

As apparently evaluated from Table 1, the organic EL devices of Examples1 to 12 have enhanced efficiencies of light emission over publicly knownComparative Compound 1 as a hole transporting material, ComparativeCompound 2 wherein N bonds directly to 3- and 6-position of carbazole,Comparative Compound 3 wherein N bonds to N of carbazole via bondinggroup and which has no substituent in its carbazole skeleton, andComparative Compound 4 that is a compound with a type wherein N directlybonds to 3-position of carbazole. As the reason, it is conceivable that3- and 9-position of carbazole skeleton in the aromatic amine derivativeof the present invention are protected and there is a bonding groupbetween carbazole skeletons and N.

Example 14

An organic EL device was fabricated in a similar procedure as Example 1except that Compound H53 was employed instead of H232 and that anarylamine compound TBDB below instead of Compound H1.

About the resultant organic EL device, luminescent color was observedand recognized as blue. Further, driving voltage was measured at initialluminance of 5000 cd/m² under a room temperature and DC constant currentdriving and as a result, it was 6.5 V.

Example 15

An organic EL device was fabricated in accordance with the sameprocedure as Example 14 except that Compound H60 was employed instead ofH53.

About the resultant organic EL device, luminescent color was observedand recognized as blue. Further, driving voltage was measured at initialluminance of 5000 cd/m² under a room temperature and DC constant currentdriving and as a result, it was 6.6 V.

Comparative Example 7

An organic EL device was fabricated in accordance with the sameprocedure as Example 14 except that H232 was employed instead of H53.

About the resultant organic EL device, luminescent color was observedand recognized as blue. Further, driving voltage was measured at initialluminance of 5000 cd/m² under a room temperature and DC constant currentdriving and as a result, it was 7.2 V.

Comparative Example 8

An organic EL device was fabricated in accordance with the sameprocedure as Example 14 except that Comparative Compound 4 was employedinstead of H53.

About the resultant organic EL device, luminescent color was observedand recognized as blue. Further, driving voltage was measured at initialluminance of 5000 cd/m² under a room temperature and DC constant currentdriving and as a result, it was 7.3 V.

As described above, the employment of the aromatic amine of the presentinvention for a hole injecting layer was proved to be effective inreducing the driving voltage.

INDUSTRIAL APPLICABILITY

As described in detail above, the organic EL device employing thearomatic amine derivative of the present invention as materials for theorganic EL device, particularly as a hole transporting material or ahole injecting material has an enhanced efficiency of light emission andis highly practical. Therefore, the organic EL device of the presentinvention is useful for a planar light emitting member for walltelevisions and a light source for a backlight of displays.

What is claimed is:
 1. An organic electroluminescence device whichcomprises one or more organic thin film layers including at least onelight emitting layer sandwiched between a cathode and an anode, whereinat least one of the organic thin film layers includes a holetransporting layer, and the hole transporting layer comprises at leastone aromatic amine derivative represented by the following generalformulae (1-d)

wherein L₁ represents an unsubstituted phenylene or a phenylene groupsubstituted with one or more groups selected from the group consistingof an alkyl group, an alkenyl group, an alkynyl group, an amino group,an alkoxy group, an aryloxy group, an acyl group, an alkoxycarbonylgroup, an aryloxycarbonyl group, an acyloxy group, an acylamino group,an alkoxycarbonylamino group, an aryloxycarbonylamino group, asulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthiogroup, an arylthio group, a sulfonyl group, a sulfonyl group, a ureidegroup, a phosphoricamide group, a hydroxy group, a mercapto group, ahalogen atom, a cyano group, a sulfo group, a carboxyl group, a nitrogroup, a hydroxamic acid group, a sulfino group, a hydrazino group, animino group, a heterocyclic group, and a silyl group; R₁ represents anunsubstituted phenyl group or a phenyl group substituted with one ormore groups selected from the group consisting of an alkyl group, analkenyl group, an alkynyl group, an amino group, an alkoxy group, anaryloxy group, an acyl group, an alkoxycarbonyl group, anaryloxycarbonyl group, an acyloxy group, an acylamino group, analkoxycarbonylamino group, an aryloxycarbonylamino group, asulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthiogroup, an arylthio group, a sulfonyl group, a sulfonyl group, a ureidegroup, a phosphoricamide group, a hydroxy group, a mercapto group, ahalogen atom, a cyano group, a sulfo group, a carboxyl group, a nitrogroup, a hydroxamic acid group, a sulfino group, a hydrazino group, animino group, a heterocyclic group, and a silyl group; R₂ represents ahydrogen atom; Ar₇ and Ar₈ each independently represents anunsubstituted phenylene group or a phenylene group substituted with oneor more groups selected from the group consisting of an alkyl group, analkenyl group, an alkynyl group, an amino group, an alkoxy group, anaryloxy group, an acyl group, an alkoxycarbonyl group, anaryloxycarbonyl group, an acyloxy group, an acylamino group, analkoxycarbonylamino group, an aryloxycarbonylamino group, asulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthiogroup, an arylthio group, a sulfonyl group, a sulfonyl group, a ureidegroup, a phosphoricamide group, a hydroxy group, a mercapto group, ahalogen atom, a cyano group, a sulfo group, a carboxyl group, a nitrogroup, a hydroxamic acid group, a sulfino group, a hydrazino group, animino group, a heterocyclic group, and a silyl group; Ar₉ represents anunsubstituted phenylene group or a phenylene group substituted with oneor more groups selected from the group consisting of an alkyl group, analkenyl group, an alkynyl group, an amino group, an alkoxy group, anaryloxy group, an acyl group, an alkoxycarbonyl group, anaryloxycarbonyl group, an acyloxy group, an acylamino group, analkoxycarbonylamino group, an aryloxycarbonylamino group, asulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthiogroup, an arylthio group, a sulfonyl group, a sulfonyl group, a ureidegroup, a phosphoricamide group, a hydroxy group, a mercapto group, ahalogen atom, a cyano group, a sulfo group, a carboxyl group, a nitrogroup, a hydroxamic acid group, a sulfino group, a hydrazino group, animino group, a heterocyclic group, and a silyl group; and Ar₁₀ is anunsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophenylgroup; wherein the number of a carbazole structure in the aromatic aminederivative represented by the general formula (1-d) is 1 or
 2. 2. Theorganic electroluminescence device according to claim 1, wherein Ar₉represents an unsubstituted phenyl group.
 3. The organicelectroluminescence device according to claim 1, wherein L₁ is anunsubstituted phenylene group.
 4. The organic electroluminescence deviceaccording to claim 1, wherein the substituent for each groups of L₁, Ar₇to Ar₉ and R₁ in the general formulae (1-d) each independentlyrepresents alkyl group having 1 to 20 carbon atoms, alkenyl group having2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, aminogroup having 0 to 20 carbon atoms, alkoxy group having 1 to 20 carbonatoms, aryloxy group having 6 to 20 carbon atoms, acyl group having 1 to20 carbon atoms, alkoxycarbonyl group having 2 to 20 carbon atoms,aryloxycarbonyl group having 7 to 20 carbon atoms, acyloxy group having2 to 20 carbon atoms, acylamino group having 2 to 20 carbon atoms,alkoxycarbonylamino group having 2 to 20 carbon atoms,aryloxycarbonylamino group having 7 to 20 carbon atoms, sulfonylaminogroup having 1 to 20 carbon atoms, sulfamoyl group having 0 to 20 carbonatoms, carbamoyl group having 1 to 20 carbon atoms, alkylthio grouphaving 1 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms,sulfonyl group having 1 to 20 carbon atoms, sulfinyl group having 1 to20 carbon atoms, ureide group having 1 to 20 carbon atoms,phosphoricamide group having 1 to 20 carbon atoms, hydroxy group,mercapto group, halogen atom, cyano group, sulfo group, carboxyl group,nitro group; hydroxamic acid group, sulfino group, hydrazino group,imino group, heterocyclic group having 1 to 30 carbon atoms, silyl grouphaving 3 to 40 carbon atoms.
 5. The organic electroluminescence deviceaccording to claim 1, wherein the aromatic amine derivative according toformula (1-d) is contained as an essential component in the holetransporting layer.
 6. The organic electroluminescence device accordingto claim 1, wherein the light emitting layer comprises at least onearomatic amine derivative represented by formula (1-d).
 7. The organicelectroluminescence device according to claim 1, wherein each of L₁, Ar₇to Ar₉ and R₁ in the general formulae (1-d) is an unsubstituted phenylor phenylene group.
 8. The organic electroluminescence device accordingto claim 1, wherein the substituent for each groups of L₁, Ar₇ to Ar₉and R₁ in the general formulae (1-d) is selected from the groupconsisting of an alkyl group having 1 to 20 carbon atoms, an amino grouphaving 0 to 20 carbon atoms, a halogen atom, a cyano group, a sulfogroup, a nitro group, a heterocyclic group having 1 to 30 carbon atoms,and a silyl group having 3 to 40 carbon atoms.
 9. An organicelectroluminescence device which comprises one or more organic thin filmlayers including at least one light emitting layer sandwiched between acathode and an anode, wherein at least one of the organic thin filmlayers includes a hole injecting layer, and the hole injecting layercomprises at least one aromatic amine derivative represented by thefollowing general formulae (1-d)

wherein L₁ represents an unsubstituted phenylene or a phenylene groupsubstituted with one or more groups selected from the group consistingof an alkyl group, an alkenyl group, an alkynyl group, an amino group,an alkoxy group, an aryloxy group, an acyl group, an alkoxycarbonylgroup, an aryloxycarbonyl group, an acyloxy group, an acylamino group,an alkoxycarbonylamino group, an aryloxycarbonylamino group, asulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthiogroup, an arylthio group, a sulfonyl group, a sulfonyl group, a ureidegroup, a phosphoricamide group, a hydroxy group, a mercapto group, ahalogen atom, a cyano group, a sulfo group, a carboxyl group, a nitrogroup, a hydroxamic acid group, a sulfino group, a hydrazino group, animino group, a heterocyclic group, and a silyl group; R₁ represents anunsubstituted phenyl group or a phenyl group substituted with one ormore groups selected from the group consisting of an alkyl group, analkenyl group, an alkynyl group, an amino group, an alkoxy group, anaryloxy group, an acyl group, an alkoxycarbonyl group, anaryloxycarbonyl group, an acyloxy group, an acylamino group, analkoxycarbonylamino group, an aryloxycarbonylamino group, asulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthiogroup, an arylthio group, a sulfonyl group, a sulfonyl group, a ureidegroup, a phosphoricamide group, a hydroxy group, a mercapto group, ahalogen atom, a cyano group, a sulfo group, a carboxyl group, a nitrogroup, a hydroxamic acid group, a sulfino group, a hydrazino group, animino group, a heterocyclic group, and a silyl group; R₂ represents ahydrogen atom; Ar₇ and Ar₈ each independently represents anunsubstituted phenylene group or a phenylene group substituted with oneor more groups selected from the group consisting of an alkyl group, analkenyl group, an alkynyl group, an amino group, an alkoxy group, anaryloxy group, an acyl group, an alkoxycarbonyl group, anaryloxycarbonyl group, an acyloxy group, an acylamino group, analkoxycarbonylamino group, an aryloxycarbonylamino group, asulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthiogroup, an arylthio group, a sulfonyl group, a sulfonyl group, a ureidegroup, a phosphoricamide group, a hydroxy group, a mercapto group, ahalogen atom, a cyano group, a sulfo group, a carboxyl group, a nitrogroup, a hydroxamic acid group, a sulfino group, a hydrazino group, animino group, a heterocyclic group, and a silyl group; Ar₉ represents anunsubstituted phenylene group or a phenylene group substituted with oneor more groups selected from the group consisting of an alkyl group, analkenyl group, an alkynyl group, an amino group, an alkoxy group, anaryloxy group, an acyl group, an alkoxycarbonyl group, anaryloxycarbonyl group, an acyloxy group, an acylamino group, analkoxycarbonylamino group, an aryloxycarbonylamino group, asulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthiogroup, an arylthio group, a sulfonyl group, a sulfonyl group, a ureidegroup, a phosphoricamide group, a hydroxy group, a mercapto group, ahalogen atom, a cyano group, a sulfo group, a carboxyl group, a nitrogroup, a hydroxamic acid group, a sulfino group, a hydrazino group, animino group, a heterocyclic group, and a silyl group; and Ar₁₀ is anunsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophenylgroup; wherein the number of a carbazole structure in the aromatic aminederivative represented by the general formula (1-d) is 1 or
 2. 10. Theorganic electroluminescence device according to claim 9, wherein Ar₉represents an unsubstituted phenyl group.
 11. The organicelectroluminescence device according to claim 9, wherein L₁ is anunsubstituted phenylene group.
 12. The organic electroluminescencedevice according to claim 9, wherein the substituent for each groups ofL₁, Ar₇ to Ar₉ and R₁ in the general formulae (1-d) each independentlyrepresents alkyl group having 1 to 20 carbon atoms, alkenyl group having2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, aminogroup having 0 to 20 carbon atoms, alkoxy group having 1 to 20 carbonatoms, aryloxy group having 6 to 20 carbon atoms, acyl group having 1 to20 carbon atoms, alkoxycarbonyl group having 2 to 20 carbon atoms,aryloxycarbonyl group having 7 to 20 carbon atoms, acyloxy group having2 to 20 carbon atoms, acylamino group having 2 to 20 carbon atoms,alkoxycarbonylamino group having 2 to 20 carbon atoms,aryloxycarbonylamino group having 7 to 20 carbon atoms, sulfonylaminogroup having 1 to 20 carbon atoms, sulfamoyl group having 0 to 20 carbonatoms, carbamoyl group having 1 to 20 carbon atoms, alkylthio grouphaving 1 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms,sulfonyl group having 1 to 20 carbon atoms, sulfinyl group having 1 to20 carbon atoms, ureido group having 1 to 20 carbon atoms,phosphoricamide group having 1 to 20 carbon atoms, hydroxy group,mercapto group, halogen atom, cyano group, sulfo group, carboxyl group,nitro group; hydroxamic acid group, sulfino group, hydrazino group,imino group, heterocyclic group having 1 to 30 carbon atoms, silyl grouphaving 3 to 40 carbon atoms.
 13. The organic electroluminescence deviceaccording to claim 9, wherein the aromatic amine derivative according toformula (1-d) is contained as an essential component in the holeinjecting layer.
 14. The organic electroluminescence device according toclaim 9, wherein each of L₁, Ar₇ to Ar₉ and R₁ in the general formulae(1-d) is an unsubstituted phenyl or phenylene group.
 15. The organicelectroluminescence device according to claim 9, wherein the substituentfor each groups of L₁, Ar₇ to Ar₉ and R₁ in the general formulae (1-d)is selected from the group consisting of an alkyl group having 1 to 20carbon atoms, an amino group having 0 to 20 carbon atoms, a halogenatom, a cyano group, a sulfo group, a nitro group, a heterocyclic grouphaving 1 to 30 carbon atoms, and a silyl group having 3 to 40 carbonatoms.